Binaphthalene seven-membered phosphine hetero-hydrogen silane as well as synthesis method and application thereof

Abstract

The invention provides a synthesis method and application of binaphthalene seven-membered phosphino-monohydrosilane, and belongs to the field of organic synthesis. The binaphthyl seven-membered phosphine heteromonohydro silane can be used as a chiral ligand or a chiral silicon positive ion Lewis acid catalyst for an asymmetric catalytic reaction, and can also be used as functionalized organic silicon or an organic phosphorus compound in material chemistry. The synthesis method provided by the invention is low in cost and high in efficiency, and the obtained product enantiomer is high in purity; the binaphthalene seven-membered phosphino-monohydrosilane provided by the invention is used as a chiral ligand to promote an asymmetric catalytic reaction, a target product can be obtained with high yield and high enantiomer purity, and the potential application of the binaphthalene seven-membered phosphino-monohydrosilane in transition metal catalytic chemistry is shown; the binaphthalene seven-membered phosphino-monohydrosilane provided by the invention participates in a chiral memory experiment as a chiral silicon positive ion precursor reagent, and shows potential application of the binaphthalene seven-membered phosphino-monohydrosilane in chiral silicon positive ion chemistry.

Description

Technical Field

[0001] The invention belongs to the field of organic synthesis, and in particular relates to a heptaphosphine-binaphthyl heteromonohydrosilane and a synthesis method and application thereof. Background Art

[0002] Silicon stereo monohydrogen silanes have a wide range of applications in synthetic chemistry, medicinal chemistry, and materials science, but the enantioselective synthesis of silicon-centered chiral organosilicon compounds has rarely been reported. In asymmetric synthesis, constructing silicon-centered chirality is one of the most challenging topics. Traditional methods usually require the use of chiral reagents or substrate control to synthesize enantiomer-enriched silicon-centered chiral silanes, but enantioselectivity is generally difficult to control.

[0003] Therefore, there is still an urgent need for a highly active monohydrogensilane and a method for synthesizing monohydrogensilane with good enantioselectivity. Summary of the invention

[0004] In order to solve the above technical problems, the present invention provides a heptaphosphine-binaphthyl monohydrogen silane and a synthesis method and application thereof.

[0005] In a first aspect, the present invention provides a compound represented by formula I.

[0006] A compound represented by formula I,

[0007]

[0008] Wherein, R1 and R3 are each independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;

[0009] R2 and R4 are each independently selected from H or substituted or unsubstituted aryl;

[0010] Optionally, the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2.

[0011] In some embodiments, the structure of the compound represented by Formula I is selected from the compound represented by Formula I-0 or the compound represented by Formula II-0:

[0012]

[0013] In some embodiments, the compound represented by formula II-0 is selected from the compound represented by formula II-1,

[0014]

[0015] In some embodiments, the compound represented by formula II-1 is selected from the compound represented by formula III-1 or the compound represented by formula III-2:

[0016]

[0017] Wherein Ar is a substituted or unsubstituted C6-C 20 Aryl.

[0018] In some embodiments, in the compound of Formula I, the compound of Formula I-0, the compound of Formula II-0 or the compound of Formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 alkyl.

[0019] In some embodiments, in the compound of Formula I, the compound of Formula I-0, the compound of Formula II-0 or the compound of Formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 Heteroaryl.

[0020] In some embodiments, in the compound of Formula I, the compound of Formula I-0, the compound of Formula II-0 or the compound of Formula II-1, R2 and R4 are substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 Heteroaryl; R1, R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 alkyl.

[0021] In some embodiments, in the compound of Formula I, the compound of Formula I-0, the compound of Formula II-0 or the compound of Formula II-1, R2 and R4 are substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 Heteroaryl; R1, R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl.

[0022] In some embodiments, in the compound of formula III-1, R1 and R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 alkyl.

[0023] In some embodiments, in the compound represented by formula III-1, R1 and R3 are each independently selected from substituted or unsubstituted C6-C 20Aryl, substituted or unsubstituted C6-C 20 Heteroaryl.

[0024] In some embodiments, in the compound represented by formula III-2, Ar is a substituted or unsubstituted C6-C 20 Aryl; R1, R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 alkyl.

[0025] In some embodiments, in the compound represented by formula III-2, Ar is a substituted or unsubstituted C6-C 20 Aryl; R1, R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 Heteroaryl.

[0026] In some embodiments, the C1-C 20 The alkyl group is C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, C 10 Alkyl, C 11 Alkyl, C 12 Alkyl, C 13 Alkyl, C 14 Alkyl, C 15 Alkyl, C 16 Alkyl, C 17 Alkyl, C 18 Alkyl, C 19 Alkyl or C 20 alkyl.

[0027] In some embodiments, the C1-C 10 The alkyl group is C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl or C 10 alkyl.

[0028] In some embodiments, the C6-C 20 The aryl group is C6 aryl, C7 aryl, C8 aryl, C9 aryl, C 10 Aryl, C 11 Aryl, C 12 Aryl, C 13 Aryl, C 14 Aryl, C 15 Aryl, C 16 Aryl, C 17 Aryl, C 18 Aryl, C 19 Aryl or C 20 Aryl.

[0029] In some embodiments, the C6-C 20 The heteroaryl group is C6 heteroaryl, C7 heteroaryl, C8 heteroaryl, C9 heteroaryl, C 10 Heteroaryl, C 11 Heteroaryl, C 12 Heteroaryl, C 13 Heteroaryl, C 14 Heteroaryl, C 15 Heteroaryl, C 16 Heteroaryl, C 17 Heteroaryl, C 18 Heteroaryl, C 19 Heteroaryl or C 20 Heteroaryl.

[0030] In some embodiments, the heteroaryl group has at least one heteroatom in the ring.

[0031] In some embodiments, the heteroatom comprises oxygen, sulfur, or nitrogen.

[0032] In some embodiments, in any of the above compounds (compounds represented by formula I, compounds represented by formula I-0, compounds represented by formula II-0, compounds represented by formula II-1, compounds represented by formula III-1 or compounds represented by formula III-2), R1, R2, R3, R4 or Ar are selected from the following groups: (1)

[0034] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0035] R2 and R4 are H;

[0036] R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2 2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0037] or (2)

[0039] In the compound represented by formula III-1, R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH 2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0040] or (3)

[0042] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0043] R2 and R4 are H;

[0044] R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or

[0045] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0046] or (4)

[0048] In the compound represented by formula III-1, R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are each independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphine, thiomethyl or -SiH(CH3)2;

[0049] or (5)

[0051] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0052] R2 and R4 are H;

[0053] R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0054] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0055] or (6)

[0057] In the compound represented by formula III-1,

[0058] R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0059] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0060] or (7)

[0062] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0063] R2 and R4 are H;

[0064] R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0065] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0066] or (8)

[0068] In the compound represented by formula III-1,

[0069] R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3) CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH 3. -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0070] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0071] or (9)

[0073] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0074] R2 and R4 are H;

[0075] R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl;

[0076] or (10)

[0078] In the compound represented by formula III-1,

[0079] R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl;

[0080] or (11)

[0082] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0083] R2 and R4 are H;

[0084] R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0085] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0086] or (12)

[0088] In the compound represented by formula III-1,

[0089] R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0090] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0091] or (13)

[0093] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0094] R2 and R4 are H;

[0095] R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0096] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0097] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0098] or (14)

[0100] In the compound represented by formula III-1,

[0101] R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0102] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0103] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0104] or (15)

[0106] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0107] R2 and R4 are H;

[0108] R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0109] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0110] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0111] or (16)

[0113] In the compound represented by formula III-1,

[0114] R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0115] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0116] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0117] or (17)

[0119] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0120] R2 and R4 are phenyl groups;

[0121] R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2 2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl;

[0122] or (18)

[0124] In the compound represented by formula III-2, Ar is phenyl;

[0125] R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2 2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl;

[0126] or (19)

[0128] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0129] R2 and R4 are phenyl groups;

[0130] R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are each independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0131] or (20)

[0133] In the compound represented by formula III-2, Ar is phenyl;

[0134] R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are each independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0135] or (twenty one)

[0137] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0138] R2 and R4 are phenyl groups;

[0139] R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl;

[0140] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0141] or (twenty two)

[0143] In the compound represented by formula III-2, Ar is phenyl;

[0144] R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl;

[0145] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0146] or (twenty three)

[0148] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0149] R2 and R4 are phenyl groups;

[0150] R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl;

[0151] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0152] or (twenty four)

[0154] In the compound represented by formula III-2, Ar is phenyl;

[0155] R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3 )CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2 CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl;

[0156] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0157] or (25)

[0159] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0160] R2 and R4 are phenyl groups;

[0161] R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl;

[0162] or (26)

[0164] In the compound represented by formula III-2, Ar is phenyl; R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl;

[0165] or (27)

[0167] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0168] R2 and R4 are phenyl groups;

[0169] R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0170] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0171] or (28)

[0173] In the compound represented by formula III-2, Ar is phenyl; R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0174] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0175] or (29)

[0177] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0178] R2 and R4 are phenyl groups;

[0179] R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0180] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0181] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0182] or (30)

[0184] In the compound represented by formula III-2, Ar is phenyl;

[0185] R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0186] R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0187] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0188] or (31)

[0190] Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1,

[0191] R2 and R4 are phenyl groups;

[0192] R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0193] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0194] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2;

[0195] or (32)

[0197] In the compound represented by formula III-2, Ar is phenyl;

[0198] R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl;

[0199] R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or

[0200] The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2.

[0201] In some embodiments, the structure of the compound of Formula I is selected from the compound of Formula III-1 or the compound of Formula III-3:

[0202]

[0203] in,

[0204] R1 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing a F substituent or phenyl containing a methoxy substituent; R3 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]

[0205] Thiphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted terphenyl; the substitution means that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2.

[0206] In some embodiments, in the compound represented by formula III-1 or the compound represented by formula III-3, R1 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing one F substituent or phenyl containing one methoxy substituent; R3 is unsubstituted phenyl, unsubstituted naphthyl, unsubstituted anthracenyl, unsubstituted biphenyl, unsubstituted triphenylphosphine, unsubstituted quinolyl, unsubstituted diphenyl ether, unsubstituted dibenzo[b,d]thienyl, unsubstituted inter-terphenyl, unsubstituted ortho-terphenyl, unsubstituted para-terphenyl, phenyl containing one F substituent, phenyl containing one or two methoxy substituents, phenyl containing one trifluoromethyl, phenyl containing three methyl groups, phenyl containing one isopropoxy substituent, phenyl containing one thiomethyl substituent, naphthyl containing one methoxy substituent or containing one -SiH(CH3)2

[0207] Substituents are phenyl.

[0208] In some embodiments, in the compound represented by formula III-1 or the compound represented by formula III-3, R3 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing a F substituent or phenyl containing a methoxy substituent; R1 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted inter-biphenyl, substituted or unsubstituted o-biphenyl or substituted or unsubstituted p-biphenyl; the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphine, thiomethyl or -SiH(CH3)2.

[0209] In some embodiments, in the compound represented by formula III-1 or the compound represented by formula III-3, R3 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing a F substituent or phenyl containing a methoxy substituent; R1 is unsubstituted phenyl, unsubstituted naphthyl, unsubstituted anthracene, unsubstituted biphenyl, unsubstituted triphenylphosphine, unsubstituted quinolyl, unsubstituted diphenyl ether, unsubstituted dibenzo[b,d]thienyl, unsubstituted inter-biphenyl, unsubstituted o-biphenyl, unsubstituted p-biphenyl, phenyl containing a F substituent, phenyl containing one or two methoxy substituents, phenyl containing a trifluoromethyl, phenyl containing three methyl groups, phenyl containing an isopropoxy substituent, phenyl containing a thiomethyl substituent, naphthyl containing a methoxy substituent or phenyl containing a -SiH(CH3)2 substituent.

[0210] In some preferred embodiments, the substitution is that one or more hydrogen atoms are independently replaced by methoxy or -SiH(CH3)2.

[0211] In some preferred embodiments, in the compound represented by formula III-1 or the compound represented by formula III-3, R1 is a phenyl group containing a methoxy substituent; R3 is a phenyl group containing a -SiH(CH3)2 substituent.

[0212] In some embodiments, the compound represented by formula I is selected from:

[0213]

[0214]

[0215]

[0216] In some preferred embodiments, the compound represented by formula I is compound 5ah.

[0217] In a second aspect, the present invention provides a method for preparing the compound described in the first aspect.

[0218] A method for preparing the compound of formula I according to the first aspect, comprising:

[0219]

[0220] Under inert gas atmosphere conditions, the compound represented by formula V-1, the compound represented by formula VII-1 and the lithiation agent undergo a first reaction in a solvent to obtain the compound represented by formula VI-1, and then undergo a second reaction with the compound represented by formula IV or the compound represented by formula VIII, and after post-treatment, obtain the compound represented by formula I; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula I described in the first aspect.

[0221] In some embodiments, a method for preparing the compound of formula I described in the first aspect comprises:

[0222]

[0223] Under an inert gas atmosphere, the compound represented by formula V-1, the compound represented by formula VII-1 and a lithiation agent undergo a first reaction in a solvent to obtain a compound represented by formula VI-1, which then undergoes a second reaction with a compound represented by formula IV or a compound represented by formula VIII, and then is mixed with borane and stirred for reaction under an inert gas atmosphere to obtain a compound represented by formula I-5, which is then mixed with DABCO (triethylenediamine) to remove borane, and is post-treated to obtain a compound represented by formula I; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula I described in the first aspect.

[0224] In some embodiments, the compound represented by Formula I is selected from the compound represented by Formula II-0, and the preparation method of the compound represented by Formula II-0 comprises:

[0225]

[0226] Under inert gas atmosphere conditions, the compound represented by formula V-2, the compound represented by formula VII-1 and the lithiation agent undergo a third reaction in a solvent to obtain a compound represented by formula VI-2, and then undergo a fourth reaction with the compound represented by formula IV or the compound represented by formula VIII, and after post-treatment, obtain a compound represented by formula II-0; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by II-0 described in the first aspect.

[0227] In some embodiments, the compound represented by Formula I is selected from the compound represented by Formula II-0, and the preparation method of the compound represented by Formula II-0 comprises:

[0228]

[0229] Under an inert gas atmosphere, the compound represented by formula V-2, the compound represented by formula VII-1 and the lithiation agent undergo a third reaction in a solvent to obtain a compound represented by formula VI-2, which then undergoes a fourth reaction with the compound represented by formula IV or the compound represented by formula VIII, and then is mixed with borane and stirred for reaction under an inert gas atmosphere to obtain a compound represented by formula II-5, which is then mixed with DABCO to remove borane, and after post-treatment, a compound represented by formula II-0 is obtained; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by II-0 described in the first aspect.

[0230] In some embodiments, the compound represented by Formula I is selected from the compound represented by Formula I-0, and the preparation method of the compound represented by Formula I-0 comprises:

[0231]

[0232] Under inert gas atmosphere conditions, the compound represented by formula V-3, the compound represented by formula VII-1 and the lithiation reagent undergo a fifth reaction in a solvent to obtain a compound represented by formula VI-3, and then undergo a sixth reaction with the compound represented by formula IV or the compound represented by formula VIII, and after post-treatment, obtain a compound represented by formula I-0; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula I-0 described in the first aspect.

[0233] In some embodiments, the compound represented by Formula I is selected from the compound represented by Formula I-0, and the preparation method of the compound represented by Formula I-0 comprises:

[0234]

[0235] Under an inert gas atmosphere, the compound represented by formula V-3, the compound represented by formula VII-1 and the lithiation agent undergo a fifth reaction in a solvent to obtain a compound represented by formula VI-3, which is then reacted with the compound represented by formula IV or the compound represented by formula VIII for a sixth reaction, and optionally mixed with borane and stirred for reaction under an inert gas atmosphere to obtain a compound represented by formula I-6, which is then mixed with DABCO to remove borane, and after post-treatment, a compound represented by formula I-0 is obtained; the selection of R1, R2, R3, and R4 is respectively as shown in R1, R2, R3, and R4 in the compound represented by formula I-0 described in the first aspect.

[0236] In some embodiments, the compound represented by Formula I is selected from the compound represented by Formula II-1, and the method comprises:

[0237]

[0238] Under inert gas atmosphere conditions, the compound represented by formula V-4, the compound represented by formula VII-1 and the lithiation reagent undergo a seventh reaction in a solvent to obtain a compound represented by formula VI-4, and then undergo an eighth reaction with the compound represented by formula IV or the compound represented by formula VIII, and after post-treatment, obtain a compound represented by formula II-1; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula II-1 described in the first aspect.

[0239] In some embodiments, the compound represented by Formula I is selected from the compound represented by Formula II-1, and the method comprises:

[0240]

[0241] Under an inert gas atmosphere, the compound represented by formula V-4, the compound represented by formula VII-1 and the lithiation agent undergo a seventh reaction in a solvent to obtain a compound represented by formula VI-4, which then undergoes an eighth reaction with the compound represented by formula IV or the compound represented by formula VIII, and then is mixed with borane and stirred for reaction under an inert gas atmosphere to obtain a compound represented by formula II-6, which is then mixed with DABCO to remove borane, and after post-treatment, a compound represented by formula II-1 is obtained; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula II-1 described in the first aspect.

[0242] The arrow between P and BH3 in the compound of formula I-5, the compound of formula I-6, the compound of formula II-5 or the compound of formula II-6 represents a coordination bond.

[0243] In some embodiments, the solvent comprises tetrahydrofuran, preferably, the solvent is tetrahydrofuran and diethyl ether.

[0244] In some embodiments, the solvent is tetrahydrofuran and diethyl ether, and the volume ratio of tetrahydrofuran to diethyl ether is 1:2-2:1. In some embodiments, the solvent is tetrahydrofuran and diethyl ether, and the volume ratio of tetrahydrofuran to diethyl ether is preferably 1:1.

[0245] In some embodiments, the stirring temperature is 10° C.-40° C. In some embodiments, the stirring temperature is 15° C.-35° C. In some embodiments, the stirring temperature is 10° C., 15° C., 20° C., 25° C., 30° C., 35° C. or 40° C.

[0246] In some embodiments, the stirring time is 5-20 hours. In some embodiments, the stirring time is 10-20 hours. In some embodiments, the stirring time is 10-15 hours. In some embodiments, the stirring time is 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, 12 hours, 13 hours, 14 hours, 15 hours, 16 hours, 17 hours, 18 hours, 19 hours or 20 hours.

[0247] In some embodiments, the inert gas is at least one of nitrogen, helium, neon, argon, krypton, and xenon.

[0248] In some embodiments, the lithiation agent is at least one of n-butyllithium, sec-butyllithium, or tert-butyllithium.

[0249] In some embodiments, the compound represented by formula VIII includes at least one of quinolin-8-yllithiu (8-lithium quinolinyl) and (2-(diphenylphosphaneyl)phenyl)lithium (2-(diphenylphosphine)phenyl)lithium).

[0250] In some embodiments, the post-processing includes concentration, purification and drying.

[0251] In some embodiments, the reaction temperature of the first reaction is -84°C to -78°C, preferably -84°C.

[0252] In some embodiments, the reaction temperature of the second reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C.

[0253] In some embodiments, the molar ratio of the compound of formula V-1 to the compound of formula VII-1 is 1.0:1.0 to 1.0:3.0. In some embodiments, the molar ratio of the compound of formula V-1 to the compound of formula VII-1 is preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0. In some embodiments, the molar ratio of the compound of formula V-1 to the compound of formula VII-1 is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5 or 1.0:3.0.

[0254] In some embodiments, the molar ratio of the compound of formula V-1 to the lithiation agent is 1.0:0.5-1.0:2.0. In some embodiments, the molar ratio of the compound of formula V-1 to the lithiation agent is 1.0:1.1. In some embodiments, the molar ratio of the compound of formula V-1 to the lithiation agent is 1.0:0.5, 1.0:0.6, 1.0:0.7, 1.0:0.8, 1.0:0.9, 1.0:1.0, 1.0:1.1, 1.0:1.2, 1.0:1.3, 1.0:1.4, 1.0:1.5, 1.0:1.6, 1.0:1.7, 1.0:1.8, 1.0:1.9 or 1.0:2.0.

[0255] In some embodiments, the molar ratio of the compound represented by formula V-1 to the compound represented by formula IV is 1.0:1.0 to 1.0:4.0, preferably

[0256] In some embodiments, the molar ratio of the compound of formula V-1 to the compound of formula IV is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5, 1.0:3.0, 1.0:3.5 or 1.0:4.0.

[0257] In some embodiments, the molar ratio of the compound of formula V-1 to the compound of formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5. In some embodiments, the molar ratio of the compound of formula V-1 to the compound of formula VIII is 1.0:1.0, 1.0:2.0, 1.0:3.0, 1.0:4.0 or 1.0:5.0.

[0258] In some embodiments, 0.1 mmol-1.0 mmol or 0.2 mmol of the compound of formula V-1 is added per 1 mL of the solvent. In some embodiments, 0.1 mmol, 0.2 mmol, 0.3 mmol, 0.4 mmol, 0.5 mmol, 0.6 mmol, 0.7 mmol, 0.8 mmol, 0.9 mmol or 1.0 mmol of the compound of formula V-1 is added per 1 mL of the solvent.

[0259] In some embodiments, the molar ratio of the compound of formula V-1 to borane is 1:1-1:10 or 1:4. In some embodiments, the molar ratio of the compound of formula V-1 to borane is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0260] In some embodiments, the molar ratio of the compound of formula V-1 to DABCO is 1:1-1:10 or 1:6. In some embodiments, the molar ratio of the compound of formula V-1 to DABCO is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0261] In some embodiments, the reaction temperature of the third reaction is -84°C to -78°C, preferably -84°C.

[0262] In some embodiments, the reaction temperature of the fourth reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C.

[0263] In some embodiments, the molar ratio of the compound of formula V-2 to the compound of formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0. In some embodiments, the molar ratio of the compound of formula V-2 to the compound of formula VII-1 is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5 or 1.0:3.0.

[0264] In some embodiments, the molar ratio of the compound of formula V-2 to the lithiation agent is 1.0:0.5-1.0:2.0 or 1.0:1.1. In some embodiments, the molar ratio of the compound of formula V-2 to the lithiation agent is 1.0:0.5, 1.0:0.6, 1.0:0.7, 1.0:0.8, 1.0:0.9, 1.0:1.0, 1.0:1.1, 1.0:1.2, 1.0:1.3, 1.0:1.4, 1.0:1.5, 1.0:1.6, 1.0:1.7, 1.0:1.8, 1.0:1.9 or 1.0:2.0.

[0265] In some embodiments, the molar ratio of the compound of formula V-2 to the compound of formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0. In some embodiments, the molar ratio of the compound of formula V-2 to the compound of formula IV is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5, 1.0:3.0, 1.0:3.5 or 1.0:4.0.

[0266] In some embodiments, the molar ratio of the compound of formula V-2 to the compound of formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5. In some embodiments, the molar ratio of the compound of formula V-2 to the compound of formula VIII is 1.0:1.0, 1.0:2.0, 1.0:3.0, 1.0:4.0 or 1.0:5.0.

[0267] In some embodiments, 0.1 mmol-1.0 mmol or 0.2 mmol of the compound of formula V-2 is added per 1 mL of the solvent. In some embodiments, 0.1 mmol, 0.2 mmol, 0.3 mmol, 0.4 mmol, 0.5 mmol, 0.6 mmol, 0.7 mmol, 0.8 mmol, 0.9 mmol or 1.0 mmol of the compound of formula V-2 is added per 1 mL of the solvent.

[0268] In some embodiments, the molar ratio of the compound of formula V-2 to borane tetrahydrofuran is 1:1-1:10 or 1:4. In some embodiments, the molar ratio of the compound of formula V-2 to borane tetrahydrofuran is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0269] In some embodiments, the molar ratio of the compound of formula V-2 to DABCO is 1:1-1:10 or 1:6. In some embodiments, the molar ratio of the compound of formula V-2 to DABCO is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0270] In some embodiments, the reaction temperature of the fifth reaction is -84°C to -78°C, preferably -84°C.

[0271] In some embodiments, the reaction temperature of the sixth reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C.

[0272] In some embodiments, the molar ratio of the compound of formula V-3 to the compound of formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0. In some embodiments, the molar ratio of the compound of formula V-3 to the compound of formula VII-1 is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5 or 1.0:3.0.

[0273] In some embodiments, the molar ratio of the compound of formula V-3 to the lithiation agent is 1.0:0.5-1.0:2.0 or 1.0:1.1. In some embodiments, the molar ratio of the compound of formula V-3 to the lithiation agent is 1.0:0.5, 1.0:0.6, 1.0:0.7, 1.0:0.8, 1.0:0.9, 1.0:1.0, 1.0:1.1, 1.0:1.2, 1.0:1.3, 1.0:1.4, 1.0:1.5, 1.0:1.6, 1.0:1.7, 1.0:1.8, 1.0:1.9 or 1.0:2.0.

[0274] In some embodiments, the molar ratio of the compound of formula V-3 to the compound of formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0. In some embodiments, the molar ratio of the compound of formula V-3 to the compound of formula IV is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5, 1.0:3.0, 1.0:3.5 or 1.0:4.0.

[0275] In some embodiments, the molar ratio of the compound of formula V-3 to the compound of formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5. In some embodiments, the molar ratio of the compound of formula V-3 to the compound of formula VIII is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5, 1.0:3.0 or 1.0:3.5.

[0276] In some embodiments, 0.1 mmol-1.0 mmol or 0.2 mmol of the compound of formula V-3 is added per 1 mL of the solvent. In some embodiments, 0.1 mmol, 0.2 mmol, 0.3 mmol, 0.4 mmol, 0.5 mmol, 0.6 mmol, 0.7 mmol, 0.8 mmol, 0.9 mmol or 1.0 mmol of the compound of formula V-3 is added per 1 mL of the solvent.

[0277] In some embodiments, the molar ratio of the compound of formula V-3 to borane is 1:1-1:10 or 1:4. In some embodiments, the molar ratio of the compound of formula V-3 to borane is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0278] In some embodiments, the molar ratio of the compound of formula V-3 to DABCO is 1:1-1:10 or 1:6. In some embodiments, the molar ratio of the compound of formula V-3 to DABCO is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0279] In some embodiments, the reaction temperature of the seventh reaction is -84°C to -78°C, preferably -84°C.

[0280] In some embodiments, the reaction temperature of the eighth reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C.

[0281] In some embodiments, the molar ratio of the compound of formula V-4 to the compound of formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0. In some embodiments, the molar ratio of the compound of formula V-4 to the compound of formula VII-1 is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5 or 1.0:3.0.

[0282] In some embodiments, the molar ratio of the compound of formula V-4 to the lithiation agent is 1.0:0.5-1.0:2.0 or 1.0:1.1. In some embodiments, the molar ratio of the compound of formula V-4 to the lithiation agent is 1.0:0.5, 1.0:0.6, 1.0:0.7, 1.0:0.8, 1.0:0.9, 1.0:1.0, 1.0:1.1, 1.0:1.2, 1.0:1.3, 1.0:1.4, 1.0:1.5, 1.0:1.6, 1.0:1.7, 1.0:1.8, 1.0:1.9 or 1.0:2.0.

[0283] In some embodiments, the molar ratio of the compound of formula V-4 to the compound of formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0. In some embodiments, the molar ratio of the compound of formula V-4 to the compound of formula IV is 1.0:1.0, 1.0:1.5, 1.0:2.0, 1.0:2.5, 1.0:3.0, 1.0:3.5 or 1.0:4.0.

[0284] In some embodiments, the molar ratio of the compound of formula V-4 to the compound of formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5. In some embodiments, the molar ratio of the compound of formula V-4 to the compound of formula VIII is 1.0:1.0, 1.0:2.0, 1.0:3.0, 1.0:4.0 or 1.0:5.0.

[0285] In some embodiments, 0.1 mmol-1.0 mmol or 0.2 mmol of the compound of formula V-4 is added per 1 mL of the solvent. In some embodiments, 0.1 mmol, 0.2 mmol, 0.3 mmol, 0.4 mmol, 0.5 mmol, 0.6 mmol, 0.7 mmol, 0.8 mmol, 0.9 mmol or 1.0 mmol of the compound of formula V-4 is added per 1 mL of the solvent.

[0286] In some embodiments, the molar ratio of the compound of formula V-4 to borane is 1:1-1:10 or 1:4. In some embodiments, the molar ratio of the compound of formula V-4 to borane is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0287] In some embodiments, the molar ratio of the compound of formula V-4 to DABCO is 1:1-1:10 or 1:6. In some embodiments, the molar ratio of the compound of formula V-4 to DABCO is 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9 or 1:10.

[0288] In some embodiments, the reaction temperature of the second reaction, the fourth reaction, the sixth reaction or the eighth reaction is independently gradually increased from -116 ° C to 10 ° C ~ 40 ° C, and it takes 10-12 hours to increase to 10 ° C ~ 40 ° C. In some embodiments, the reaction temperature of the second reaction, the fourth reaction, the sixth reaction or the eighth reaction is independently gradually increased from -116 ° C to 15 ° C ~ 35 ° C, and it takes 10-12 hours to increase to 15 ° C ~ 35 ° C. In some embodiments, the reaction temperature of the second reaction, the fourth reaction, the sixth reaction or the eighth reaction is independently gradually increased from -116 ° C to 20 ° C ~ 30 ° C, and it takes 10-12 hours to increase to 20 ° C ~ 30 ° C. In some embodiments, the reaction temperature of the second reaction, the fourth reaction, the sixth reaction or the eighth reaction is independently gradually increased from -116 ° C to 25 ° C, and it takes 10-12 hours to increase to 25 ° C.

[0289] In some embodiments, the temperature of the step of mixing with borane and stirring the reaction under an inert gas atmosphere is 0° C. to 25° C. In some embodiments, the temperature of the step of mixing with borane and stirring the reaction under an inert gas atmosphere is 0° C., 5° C., 10° C., 15° C., 20° C., or 25° C.

[0290] In some embodiments, the temperature of the step of mixing with DABCO is 25° C.-80° C. In some embodiments, the temperature of the step of mixing with DABCO is 25° C., 30° C., 35° C., 40° C., 45° C., 50° C., 55° C., 60° C., 65° C., 70° C., 75° C., or 80° C.

[0291] In a third aspect, the present invention provides an application of the compound of formula I described in the first aspect or the compound of formula I obtained by the preparation method described in the second aspect.

[0292] A use of the compound of formula I described in the first aspect or the compound of formula I obtained by the preparation method described in the second aspect in asymmetric catalytic reactions or material chemistry.

[0293] In some embodiments, a compound of formula I described in the first aspect or a compound of formula I obtained by the preparation method described in the second aspect is used as a chiral ligand or chiral silicon cation in an asymmetric catalytic reaction or as a functionalized organosilicon or organophosphorus compound in materials chemistry.

[0294] In a fourth aspect, the present invention provides a compound.

[0295] A compound comprising:

[0296] in

[0297] The selection of R1, R2, and R4 are respectively as shown in R1, R2, and R4 in the compound represented by formula I described in the first aspect;

[0298] or include

[0299]

[0300] Beneficial Effects

[0301] Compared with the prior art, the present invention has at least one of the following technical effects:

[0302] 1) The raw material dichlorosilane used in the preparation method provided by the present invention is a commercially available organic silicon raw material with low cost.

[0303] 2) The preparation method provided by the present invention has high reaction efficiency, and the obtained product has high enantiomeric purity.

[0304] 3) The reaction of the preparation method provided by the present invention can obtain two different diastereomers by different reagent introduction orders, and both can achieve high enantiomeric purity.

[0305] 4) The reaction method of the preparation method provided by the present invention can provide a good reference for the asymmetric synthesis of other highly functionalized chiral monohydrogen silanes.

[0306] 5) The compounds provided by the present invention can be used as chiral ligands or chiral silicon cations in asymmetric catalytic reactions or as functionalized organosilicon or organophosphorus compounds in material chemistry.

[0307] 6) When the compound provided by the present invention is used as a chiral ligand in an asymmetric catalytic reaction, the product has high enantiomeric purity and high product yield, and compound 5ah is preferably used.

[0308] 7) The compounds provided by the present invention are a class of potential silicon cation precursor reagents and are expected to be used in chiral silicon cation chemistry; chiral silicon cations are a class of strong chiral Lewis acid catalysts, and the compounds provided by the present invention can also be used in the field of asymmetric catalysis.

[0309] Definition of terms

[0310] Unless otherwise indicated, the following terms and phrases as used herein are intended to have the following meanings:

[0311] In the present invention, expressions such as "compound I" and "compound represented by formula I" refer to the same compound.

[0312] In the present invention, the meanings of the atoms in the compound structure are as follows: F represents fluorine, Cl represents chlorine, and Br represents bromine.

[0313] The term "and / or" should be understood to mean any one of the optional items or a combination of any two or more of the optional items.

[0314] The term "optional", "optional" or "optionally" means that the event or situation described later may but does not necessarily occur. For example, "optionally, the heteroatom in the heterocycle includes at least one selected from nitrogen, oxygen, and sulfur" means that the situation of "the heteroatom in the heterocycle includes at least one selected from nitrogen, oxygen, and sulfur" may exist or not exist.

[0315] The term "V:V" means volume ratio.

[0316] In the present invention, 1, 2, 3, 4 in the lower right corner of R1, R2, R3, R4 represent numbers, not the number.

[0317] In the present invention, "Me" represents a methyl group; "Ph" represents a phenyl group; and "n-Bu" represents a n-butyl group.

[0318] In the present invention, "room temperature" refers to ambient temperature, which is from about 10°C to about 40°C. In some embodiments, "room temperature" refers to a temperature from about 20°C to about 30°C; in other embodiments, "room temperature" refers to a temperature from about 25°C to about 30°C; in still other embodiments, "room temperature" refers to 10°C, 15°C, 20°C, 25°C, 30°C, 35°C, 40°C, etc.

[0319] "Alkyl" is a hydrocarbon containing positive carbon atoms, secondary carbon atoms, tertiary carbon atoms, or cyclic carbon atoms. For example, an alkyl group can have 1 to 10 carbon atoms (i.e., C1-C 10alkyl), 1 to 8 carbon atoms (i.e., C1-C8 alkyl), or 1 to 6 carbon atoms (i.e., C1-C6 alkyl). Examples of suitable alkyl groups include, but are not limited to, methyl (Me, -CH3), ethyl (Et, -CH2CH3), 1-propyl (i-Pr, i-propyl, -CH2CH2CH3), 2-propyl (i-Pr, i-propyl, -CH(CH3)2), 1-butyl (n-Bu, n-butyl, -CH2CH2CH2CH3), 2-methyl-1-propyl (i-Bu, i-butyl, -CH2CH(CH3)2), 2-butyl (s-Bu, s-butyl, -CH (CH3)CH2CH3), 2-methyl-2-propyl (t-Bu, t-butyl, -C(CH3)3), 1-pentyl (n-pentyl, -CH2CH2CH2CH2CH3), 2-pentyl (-CH(CH3)CH2CH2CH3), 3-pentyl (-CH(CH2CH3)2), 2-methyl-2-butyl (-C(CH3)2CH2CH3), 3-methyl-2-butyl (-CH(CH3)CH(CH3)2), 3-methyl-1-butyl ( -CH2CH2CH(CH3)2), 2-methyl-1-butyl (-CH2CH(CH3)CH2CH3), 1-hexyl (-CH2CH2CH2CH2CH2CH3), 2-hexyl (-CH(CH3)CH2CH2CH2CH3), 3-hexyl (-CH(CH2CH3)(CH2CH2CH3)), 2-methyl-2-pentyl (-C(CH3)2CH2CH2CH3), 3-methyl-2-pentyl (-CH(CH3)CH (CH3)CH2CH3), 4-methyl-2-pentyl (-CH(CH3)CH2CH(CH3)2), 3-methyl-3-pentyl (-C(CH3)(CH2CH3)2), 2-methyl-3-pentyl (-CH(CH2CH3)CH(CH3)2), 2,3-dimethyl-2-butyl (-C(CH3)2CH(CH3)2), 3,3-dimethyl-2-butyl (-CH(CH3)C(CH3)3 and octyl (-(CH2)7CH3).

[0320] The term "carbocyclyl" or "carbocycle" refers to a monovalent or polyvalent non-aromatic saturated or partially unsaturated monocyclic, bicyclic or tricyclic system containing 3-12 carbon atoms.Carbobicyclic groups include spirocarbobicyclic groups and fused carbobicyclic groups, and suitable carbocyclyl groups include, but are not limited to, cycloalkyl, cycloalkenyl and cycloalkynyl. Examples of carbocyclyl groups further include cyclopropyl, cyclobutyl, cyclopentyl, 1-cyclopentyl-1-alkenyl, 1-cyclopentyl-2-alkenyl, 1-cyclopentyl-3-alkenyl, cyclohexyl, 1-cyclohexyl-1-alkenyl, 1-cyclohexyl-2-alkenyl, 1-cyclohexyl-3-alkenyl, cyclohexadienyl, cycloheptyl, cyclohexyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, etc. When the structure clearly requires a linking group, the Markush variables listed for the group should be understood as a linking group. For example, if the structure requires a linking group and the Markush group definition for that variable lists "carbocyclyl," it is understood that the "carbocyclyl" represents the linking carbocyclylene group.

[0321] The term "cycloalkyl" refers to a monovalent or polyvalent saturated monocyclic, bicyclic or tricyclic ring system containing 3 to 12 carbon atoms. In one embodiment, the cycloalkyl contains 3 to 12 carbon atoms; in another embodiment, the cycloalkyl contains 3 to 8 carbon atoms; in yet another embodiment, the cycloalkyl contains 3 to 6 carbon atoms. The cycloalkyl groups may be independently unsubstituted or substituted with one or more substituents described herein.

[0322] "Aryl" means an aromatic hydrocarbon group derived by removing a hydrogen atom from a single carbon atom of a parent aromatic ring system. For example, an aryl group can have 6 to 20 carbon atoms, 6 to 14 carbon atoms, or 6 to 10 carbon atoms. Typical aryl groups include, but are not limited to, groups derived from benzene (e.g., phenyl), substituted benzenes, naphthalene, anthracene, biphenyl, and the like, and the like.

[0323] The term "substituted" refers to alkyl, aryl, arylalkyl, heterocyclyl, heteroaryl, carbocyclyl, etc. For example, "substituted C1-C 10 Alkyl", "substituted C6-C 20 Aryl", "substituted arylalkyl", "substituted C1-C 20 "Heterocycle" and "substituted carbocyclyl" refer to C1-C2- 10 Alkyl, C6-C 20 Aryl, Arylalkyl, C1-C 20 Heterocycle, alkylamino, carbocyclyl. Unless otherwise indicated, when the term "substituted" is used in conjunction with a group having two or more moieties capable of substitution, such as arylalkyl, the substituents may be attached to the aryl portion, the alkyl portion, or both.

[0324] The term "unsubstituted" refers to alkyl, aryl, arylalkyl, heterocyclyl, heteroaryl, carbocyclyl, etc. For example, "unsubstituted C1-C 10 Alkyl", "unsubstituted C6-C 20 Aryl", "unsubstituted arylalkyl", "unsubstituted C1-C 20 "Heterocycle" and "unsubstituted carbocyclic group" refer to C1-C2- 10 Alkyl, C6-C 20 Aryl, Arylalkyl, C1-C 20 Heterocyclic, alkylamino, carbocyclic.

[0325] As used herein, "heterocycle" or "heterocyclyl" includes, by way of example and without limitation, those heterocycles described in Paquette, Leo A.: Principles of Modern Heterocyclic Chemistry (WA Benjamin, New York, 1968), in particular Chapters 1, 3, 4, 6, 7 and 9: The Chemistry of Heterocyclic Compounds, A Series of Monographs^ (John Wiley & Sons, New York, 1950 to present), in particular Volumes 13, 14, 16, 19 and 28 and J. Am. Chem. Soc. (1960) 82:5566. In a particular embodiment of the invention, "heterocycle" includes "carbocycles" as defined herein, in which one or more (e.g. 1, 2, 3 or 4) carbon atoms have been replaced by heteroatoms (e.g. O, N or S). The term "heterocycle" or "heterocyclyl" includes saturated rings, partially unsaturated rings and aromatic rings (i.e. heteroaromatic rings). Substituted heterocyclyl groups include, for example, heterocycles substituted with any of the substituents disclosed herein including carbonyl.

[0326] Examples of heterocyclic rings include, by way of example and not limitation, pyridyl, dihydropyridyl, tetrahydropyridyl (piperidinyl), thiazolyl, tetrahydrothiophenyl, thiooxytetrahydrothiophenyl, pyrimidinyl, furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, tetrazolyl, benzofuranyl, thiazolidine, indolyl, indolene, quinolyl, isoquinolyl, benzimidazolyl, piperidine 4-piperidinyl, pyrrolidinyl, 2-pyrrolidinyl, pyrrolinyl, tetrahydrofuranyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, octahydroisoquinolinyl, azoctinyl, triazine, 6H-1,2,5-thiadiazinyl, 2H,6H-1,5,2-dithiazinyl, thienyl, thianthrenyl, pyranyl, isobenzofuranyl, furanyl, chromenyl, xanthenyl, phenolic flavonyl, 2H-pyrrolyl, isothiazolyl, isoxazolyl, pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, 3H-indolyl, 1H-indazolyl, purinyl, 4H-quinolizinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, 4aH-carbazolyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl , pyrimidinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, furazanyl, phenoxazinyl, isochromanyl, chromanyl, imidazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, piperazinyl, indolinyl, isoindolinyl, quinuclidinyl, morpholinyl, oxazolidinyl, benzotriazolyl, benzisoxazolyl, oxindolyl, benzoxazolinyl, isatoacyl, and bis-tetrahydrofuranyl.

[0327] "Heteroaryl" refers to an aromatic heterocyclic radical having at least one heteroatom in the ring. Non-limiting examples of suitable heteroatoms that may be included on the aromatic ring include oxygen, sulfur or nitrogen. Non-limiting examples of heteroaryl rings include all those aromatic rings listed in the definition of "heterocyclic radical", including pyridyl, pyrrolyl, oxazolyl, indolyl, isoindolyl, purinyl, furyl, thienyl, benzofuranyl, benzothienyl, carbazolyl, imidazolyl, thiazolyl, isoxazolyl, pyrazolyl, isothiazolyl, quinolyl, isoquinolyl, pyridazinyl, pyrimidinyl, pyrazolyl etc.

[0328] The compounds described in formula I may have chiral centers, such as chiral carbons. The compounds described in formula I therefore include racemic mixtures of all stereoisomers, including enantiomers, diastereomers and atropisomers. In addition, the compounds described in the present invention include optical isomers enriched or separated at any or all asymmetric chiral atoms. In other words, chiral centers similar to the description are provided in the form of chiral isomers or racemic mixtures. Racemic and diastereomeric mixtures, as well as separate or synthesized, substantially free of their enantiomers or diastereomeric partners, are within the scope of the present invention. Racemic mixtures are separated into their separate, substantially optically pure isomers by known techniques, such as separation of diastereomeric salts formed with optically active auxiliary agents (such as acids or bases), which are then converted back to optically active substances. In most cases, starting from the appropriate stereoisomers of the desired raw materials, the desired optical isomers are synthesized by stereospecific reactions.

[0329] Whenever a compound described herein is substituted with more than one of the same designated group (eg, "R" or "R1"), it is understood that these groups may be the same or different, ie, each group is independently selected. DETAILED DESCRIPTION

[0330] In order to enable those skilled in the art to better understand the technical solution of the present invention, some non-limiting embodiments are further disclosed below to further illustrate the present invention in detail.

[0331] The reagents used in the present invention can be purchased from the market or prepared by the method described in the present invention.

[0332] In the present invention, μM represents micromoles per liter (μmol / L); M represents mol / L; mM represents mmol / L; equiv represents equivalent; and n-BuLi represents n-butyllithium.

[0333] In the present invention, unless otherwise specified, when describing the dr of a compound, the dr value represents the ratio of the described compound to its diastereomer. For example, the dr value of compound 5a in Experiment 1 in Table 1 of Example 44 is 7:1, which means that the content ratio of compound 5a to its diastereomer is 7:1, and the dr values ​​of other compounds are similar.

[0334] de stands for diastereomeric excess, which is defined as the percentage of the excess of one isomer a over the other isomer b in a diastereomeric mixture.

[0335] ee stands for enantiomeric excess, which is defined as the percentage of the excess of one isomer a over the other isomer b in a mixture of enantiomers.

[0336] Unless otherwise specified, the meanings of the reagents described in the present invention are commonly understood in the art.

[0337] In the present invention, "CyMgBr" means cyclohexylmagnesium bromide; "THF" means tetrahydrofuran; "DABCO" means triethylenediamine. "BH3" or "H3B" means borane; "CCl4" means tetrachloromethane; "TMEDA" means tetramethylethylenediamine; "Et2O" means diethyl ether; "n-BuLi" means n-butyllithium. "PE" means petroleum ether; "EA" means ethyl acetate. "DCM" means dichloromethane. "TLC" means thin layer chromatography.

[0338] The raw materials used in the present invention, the provided compounds, and the application of the provided compounds can be carried out according to the following experimental procedures:

[0339] Preparation of dichlorosilane compounds

[0340]

[0341] Experimental Procedure C:

[0342] To a solution of SiHCl3 (4.6 mL, 45.0 mmol, 1.5 equiv) in THF (50 mL) at -78°C was added a Grignard reagent (30.0 mmol, 1.0 equiv) dropwise. The reaction was stirred at -78°C for 1 hour and then warmed to room temperature for 12 hours. The reaction mixture was then evaporated to dryness in vacuo to produce a colorless oil with a large amount of solid inorganic salts. n-Hexane (50 mL) was added to the crude product, and the resulting slurry was sonicated and filtered to remove the inorganic salts, then washed with n-hexane (2×50 mL). The clear colorless filtrate was evaporated to dryness in vacuo to give a translucent brown oil, which was distilled to give the pure dichlorosilane compound.

[0343] Preparation of Axially Chiral Binaphthyl Heptaphosphine Monohydrogen Silane

[0344]

[0345] Experimental Procedure D:

[0346] Phosphorus-containing bromide 1a / 1b (1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. R1SiHCl2 (2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. R3-MgBr or R3-Li (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to obtain the crude reaction mixture. 1 H NMR and 31 P NMR analysis was used to characterize the crude axial chiral binaphthyl heptaphosphine heteromonohydrosilane (Compound 5). The reaction crude axial chiral binaphthyl heptaphosphine heteromonohydrosilane was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equivalents) was added under an argon atmosphere and stirred at room temperature for 12 hours; concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5·BH3, and then DABCO (6.0 equivalents) was used in toluene (5.0 mL) at 50°C for 6 hours to remove BH3 to obtain a crude product, which was concentrated and purified by flash silica gel column chromatography and dried to obtain the axial chiral binaphthyl heptaphosphine heteromonohydrosilane (Compound 5).

[0347] Performance of Chiral Silyl Ligands in Intermolecular Enantioselective CH Silylation

[0348]

[0349] General Procedure E: In an argon-filled glove box, [Ir(OMe)(cod)]2 (1.6 mg, 0.0025 mmol), chiral ligand (0.005 mmol) and anhydrous toluene (0.4 mL) were loaded into a dried 5 mL microwave reaction tube. After stirring at room temperature for 5-10 minutes, compound 6 (0.10 mmol, 25.5 mg), compound 7 (0.20 mmol, 27.3 mg), 3,3-dimethyl-1-butene (0.20 mmol, 16.8 mg) and toluene (0.4 mL) were added. The tube was capped and removed from the glove box. The resulting mixture was stirred at 60 °C for 12 hours. The reaction mixture was then concentrated and purified by flash silica gel column chromatography. The enantiomeric excess was determined by chiral HPLC analysis.

[0350] Example 1: Preparation of (R)-4-(2-bromophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 1a)

[0351]

[0352] Method 1:

[0353] 1-3(R)-2,2'-dimethyl-1,1'-binaphthyl (A1) (4.24 g, 15.0 mmol, 1.0 equiv), N-bromosuccinimide (NBS) (5.87 g, 33.0 mmol, 2.2 equiv) and 2,2'-azobis(2-methylpropionitrile) (AIBN) (123.2 mg, 0.75 mmol, 0.05 equiv) were refluxed in degassed CCl4 (150 mL) under argon atmosphere for 24 hours, cooled to room temperature, filtered through a celite pad, and washed with CH2Cl2. The organic layer was neutralized with saturated NaHCO3, washed with brine, dried over Na2SO4 and the solvent was removed in vacuo. The resulting residue was filtered through a silica gel pad. The solvent was removed in vacuo and the crude material was recrystallized from DCM / petroleum ether to give (R)-2,2'-bis(bromomethyl)-1,1'-binaphthyl (Compound A2) as a colorless solid (4.74 g, 72% yield).

[0354] To a solution of compound A2 (4.74 g, 10.8 mmol, 1.0 equiv) and NaH (60% in mineral oil, 1.38 g, 34.6 mmol, 3.2 equiv) in anhydrous THF (0.12 M) was added (2-bromophenyl)phosphine (2.04 g, 10.8 mmol, 1 equiv) dropwise at -78 °C under argon atmosphere. The mixture was allowed to warm to room temperature naturally and stirred at room temperature for 24 h. After the addition of additional (2-bromophenyl)phosphine (204 mg, 1.08 mmol, 0.1 equiv), the mixture was heated to reflux for 24 h. After the reaction was complete, the solvent was removed under vacuum (monitored by TLC). The residue was purified by flash column chromatography on silica gel with petroleum ether / dichloromethane (V:V) = 100 / 1 as eluent and dried to give compound 1a (white solid, 4.67 g, 93% yield).

[0355] Method 2:

[0356] n-Butyl lithium (2.5 M in n-hexane, 20 mL, 50 mmol, 2.5 equiv) was placed in a 250 mL Schlenk tube and the solvent was evaporated under high vacuum. The residue was dissolved in Et2O (60 mL) and the mixture was cooled to 0°C. A solution of (R)-2,2'-dimethyl-1,1'-binaphthyl (A1) (5.65 g, 20 mmol, 1 equiv) in Et2O (60 mL) was added dropwise, followed by TMEDA (7.8 mL, 52 mmol, 2.6 equiv). The resulting suspension was stirred at room temperature for 20 hours. The mixture was filtered under argon atmosphere and the resulting solid was washed with anhydrous n-hexane (60 mL). Drying under high vacuum gave dilithiated (R)-2,2'-dimethyl-1,1'-binaphthyl 2TMEDA (5.4 g, 51%, red solid).

[0357] A suspension of dilithiated (R)-2,2'-dimethyl-1,1'-binaphthyl·2TMEDA (5.4 g, 10.26 mmol, 1 equiv) in n-hexane (60 mL) was cooled to 0°C, (2-bromophenyl)dichlorophosphine (2.91 g, 11.29 mmol, 1.1 equiv) was added, and the resulting mixture was heated at 80°C for 2 h. The reaction was quenched by adding water and extracted with CH2Cl2, and the solvent was removed in vacuo. The residue was purified by silica gel flash column chromatography using petroleum ether / ethyl acetate (100 / 0 to 100 / 1) as eluent; dried to give compound 1a (white solid, 3.87 g, 42% yield, over 2 steps). The obtained compound 1a was measured for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0358] Characterization of the obtained compound 1a:

[0359]

[0360] 1HNMR(400MHz, CDCl3)δ7.92(d,J=8.2Hz,2H),7.88–7.80(m,1H),7.73–7.58(m,3H),7 .47–7.36(m,2H),7.30(dd,J=8.5,1.2Hz,1H),7.26–7.20(m,3H),7.16(td,J=7.6,1. 7Hz,1H),7.08(td,J=7.5,1.3Hz,1H),6.79(dt,J=7.6,1.7Hz,1H),6.73(d,J=8.3Hz, 1H),3.11(dd,J=14.3,3.7Hz,1H),2.89(dd,J=16.6,11.3Hz,1H),2.84–2.70(m,2H);

[0361] 13 CNMR (101MHz, CDCl3) δ137.61 (d, J = 25.8Hz), 134.09 (d, J = 4.6Hz), 133.85 (d, J = 2.1Hz), 133.82, 133.26,133.24,133.06,133.03(d,J=1.8Hz),132.43,132.26(d,J=2.1Hz),131.95,131.90,130. 23,128.98(d,J=29.1Hz),128.50(d,J=1.8Hz),128.44,128.32,127.74,127.63(d,J=2.5Hz),127 .15,126.85,126.75,126.12,126.02,125.31,125.02,30.36(d,J=22.7Hz),29.43(d,J=17.7Hz);

[0362] 31 PNMR (162MHz,CDCl3)δ3.07.

[0363] HRMS (ESI) m / zcalcdforC 28 H 21 BrP[M+H] + 467.0559,found467.0561.

[0364] Example 2: Preparation of (R)-4-(2-bromophenyl)-2,6-diphenyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 1b)

[0365]

[0366] (R)-2,2'-dimethyl-3,3'-diphenyl-1,1'-binaphthyl 7 (A3) (3.04 g, 7.0 mmol, 1.0 equiv), N-bromosuccinimide (NBS) (2.74 g, 15.4 mmol, 2.2 equiv) and 2,2'-azobis(2-methylpropionitrile) (AIBN) (114.9 mg, 0.7 mmol, 0.1 equiv) were refluxed in degassed benzene (35 mL) under argon atmosphere for 12 h. After cooling to room temperature, it was filtered through a celite pad and washed with CH2Cl2. The organic layer was neutralized with saturated NaHCO3, washed with brine, dried over Na2SO4 and the solvent was removed in vacuo. The resulting residue was filtered through a silica gel pad. The solvent was removed in vacuo and the crude material was recrystallized from DCM / petroleum ether (V:V) = 1:100-1:30 to give (R)-2,2'-bis(bromomethyl)-3,3'-diphenyl-1,1'-binaphthyl (A4) (colorless solid, 3.95 g, yield 95%).

[0367] To a solution of A4 (3.95 g, 6.7 mmol, 1.0 equiv) and NaH (60% in mineral oil, 0.86 g, 21.3 mmol, 3.2 equiv) in anhydrous THF (0.12 M) was added (2-bromophenyl)phosphine (1.27 g, 6.7 mmol, 1.0 equiv) dropwise at -78 °C under an argon atmosphere. The mixture was naturally warmed to room temperature and stirred at room temperature for 24 hours. After adding additional (2-bromophenyl)phosphine (127 mg, 0.67 mmol, 0.1 equiv), the mixture was heated to reflux for 24 h. After the reaction was completed, the solvent was removed under vacuum (monitored by TLC). The residue was purified by silica gel flash column chromatography using petroleum ether / dichloromethane (V:V) = 100 / 1 as eluent; dried to give a white solid product (3.38 g, 82% yield). The obtained compound 1b was taken for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0368] Characterization of compound 1b:

[0369]

[0370] 1HNMR(600MHz, CDCl3)δ7.94(d,J=8.3Hz,1H),7.90(s,1H),7.83(d,J=8.1Hz, 1H),7.70(d,J=7.5Hz,2H),7.60(s,1H),7.47(dt,J=8.1,3.7Hz,1H),7.43(t, J=7.5Hz,3H),7.38–7.18(m,9H),7.18–7.02(m,4H),6.64(d,J=7.4Hz,1H),3. 76(dd,J=14.7,3.1Hz,1H),2.89(dd,J=14.6,11.3Hz,1H),2.71–2.62(m,2H).

[0371] 13 CNMR(151MHz, CDCl3)δ141.56,141.12,140.41(d,J=2.9Hz),140.27,137.64(d,J=217.4Hz),136.75,1 35.14(d,J=4.5Hz),134.40,133.41,133.40,132.40,131.87,131.76,131.71(d,J=1.7Hz),131.38,131 .28,130.07,130.05(d,J=28.8Hz),130.04,129.65,129.46,128.90,128.33(2),128.28,127.34,126.9 2,126.90,126.77,126.63,126.12,125.96,125.77,125.44,26.02(d,J=18.4Hz),25.03(d,J=25.2Hz).

[0372] 31 PNMR (243MHz,CDCl3)δ1.18.

[0373] HRMS (ESI) m / zcalcdforC 40 H 29 BrP[M+H] + 619.1185, found 619.1186.

[0374] Example 3: Preparation of dichloro(4-methoxyphenyl)silane (Compound 2b)

[0375]

[0376] To a solution of SiHCl3 (4.6 mL, 45.0 mmol, 1.5 equiv) in THF (50 mL) was added p-MeO-C6H4MgBr (30.0 mmol, 1.0 equiv) dropwise at -78°C. The reaction was stirred at -78°C for 1 hour and then warmed to room temperature for 12 hours. The reaction mixture was then evaporated to dryness in vacuo to produce a colorless oil with a large amount of solid inorganic salts. n-Hexane (50 mL) was added to the crude product, and the resulting slurry was sonicated and filtered to remove inorganic salts, and then washed with n-hexane (2×50 mL). The transparent colorless filtrate was evaporated to dryness in vacuo to obtain a translucent brown oil, and the crude oil was distilled to obtain pure compound 2b (4.24 g, 68% yield) as a colorless oil. The obtained compound 2b was measured for hydrogen spectrum, carbon spectrum, 29 SiNMR, etc., the results are as follows:

[0377] Characterization of compound 2b:

[0378] 1 HNMR(400MHz, CDCl3)δ7.77–7.39(m,2H),6.97–6.77(m,2H),5.96–5.68(m,1H),3.81–3.62(m,3H);

[0379] 13 CNMR (101MHz, CDCl3) δ162.97,135.31,122.14,114.41,55.31;

[0380] 29 SiNMR (79MHz,CDCl3)δ-2.39.

[0381] Example 4: Preparation of dichloro(4-fluorophenyl)silane (Compound 2c)

[0382]

[0383] p-FC6H4MgBr (30.0 mmol, 1.0 equiv) was added dropwise to a solution of SiHCl3 (4.6 mL, 45.0 mmol, 1.5 equiv) in THF (50 mL) at -78 °C. The reaction was stirred at -78 °C for 1 hour and then warmed to room temperature for 12 hours. The reaction mixture was then evaporated to dryness in vacuo to produce a colorless oil with a large amount of solid inorganic salts. n-Hexane (50 mL) was added to the crude product, and the resulting slurry was sonicated and filtered to remove the inorganic salts, and then washed with n-hexane (2×50 mL). The transparent colorless filtrate was evaporated to dryness in vacuo to obtain a translucent brown oil, and the crude oil was distilled to obtain pure compound 2c (colorless oil, 3.62 g, 62% yield). The obtained compound 2c was measured for hydrogen spectrum, carbon spectrum, 19 FNMR, etc., the results are as follows:

[0384] Characterization of compound 2c:

[0385] 1 HNMR (400MHz, CDCl3) δ7.81–7.66(m,2H),7.25–7.15(m,2H),5.98(s,1H).

[0386] 13 CNMR (101MHz, CDCl3) δ165.60 (d, J = 253.6Hz), 136.01 (d, J = 8.4Hz), 127.06 (d, J = 3.7Hz), 116.17 (d, J = 20.7Hz).

[0387] 19 FNMR (376MHz,CDCl3)δ-105.69.

[0388] Example 5: Preparation of dichloro(cyclohexyl)silane (2d)

[0389]

[0390] Cyclohexyl Grignard reagent CyMgBr (30.0 mmol, 1.0 equiv) was added dropwise to a solution of SiHCl3 (4.6 mL, 45.0 mmol, 1.5 equiv) in THF (50 mL) at -78 °C. The reaction was stirred at -78 °C for 1 hour and then warmed to room temperature for 12 hours. The reaction mixture was then evaporated to dryness in vacuo to produce a colorless oil with a large amount of solid inorganic salts to obtain a crude product. n-Hexane (50 mL) was added to the crude product, and the resulting slurry was sonicated and filtered to remove the inorganic salts, and then washed with n-hexane (2×50 mL). The transparent colorless filtrate was evaporated to dryness in vacuo to obtain a translucent brown oil, and the crude oil was distilled to obtain compound 2d (colorless oil, 3.19 g, 58% yield). The obtained compound 2d was measured for hydrogen spectrum, carbon spectrum, etc., and the results are as follows:

[0391] Characterization of compound 2d:

[0392] 1 HNMR (600MHz, CDCl3) δ5.34(s,1H),1.91–1.77(m,4H),1.76–1.69(m,1H),1.36–1.24(m,5H),1.25–1.14(m,1H).

[0393] 13 CNMR(151MHz,CDCl3)δ29.51,26.99,26.36,25.29.

[0394] Example 6: Preparation of dichloro(2-methoxyphenyl)silane (Compound 2e)

[0395]

[0396] o-MeO-C6H4MgBr (30.0 mmol, 1.0 equiv) was added dropwise to a solution of SiHCl3 (4.6 mL, 45.0 mmol, 1.5 equiv) in THF (50 mL) at -78°C. The reaction was stirred at -78°C for 1 hour and then warmed to room temperature for 12 hours. The reaction mixture was then evaporated to dryness in vacuo to produce a colorless oil with a large amount of solid inorganic salts to obtain a crude product. n-Hexane (50 mL) was added to the crude product, and the resulting slurry was sonicated and filtered to remove the inorganic salts, and then washed with n-hexane (2×50 mL). The transparent colorless filtrate was evaporated to dryness in vacuo to obtain a translucent brown oil, and the crude oil was distilled to obtain compound 2e (colorless oil, 4.03 g, 65% yield). The obtained compound 2e was measured for hydrogen spectrum and carbon spectrum, and the results are as follows:

[0397] 1HNMR (400MHz, CDCl3) δ7.66 (dd, J=7.4, 1.8Hz, 1H), 7.53 (ddd, J=8.3, 7.4, 1.8Hz, 1H),7.07(td,J=7.4,0.9Hz,1H),6.92(d,J=8.4Hz,1H),5.98(s,1H),3.89(s,3H).

[0398] 13 CNMR (101MHz, CDCl3) δ164.27,135.49,134.55,121.33,119.36,110.47,55.90.

[0399] Example 7: Preparation of (4S,11bR)-4-(2-((R)-chloro(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 3a)

[0400]

[0401] Chiral phosphorus compound 1a (467.3 mg, 1 mmol, 1 equiv) and THF (5 mL) were mixed, cooled to -84 ° C (using ethyl acetate / liquid nitrogen bath), and n-BuLi (0.44 mL, 1.1 mmol, 1.1 equiv) was added dropwise under argon atmosphere; stirred at -84 ° C for 1 hour. MeSiHCl2 (210 μl, 2 mmol, 2 equiv) was added and the solution was stirred at -84 ° C for another hour. The solution was then warmed to room temperature. The solvent was removed under reduced pressure. Tetrachloroethane was used as an internal standard and the crude mixture was reacted by 1 HNMR and 31 PNMR analysis confirmed that compound 3a had a 95% yield and >99:1 dr. The obtained compound 3a was measured for hydrogen spectrum, carbon spectrum and 31 PNMR et al., the results are as follows:

[0402] Characterization of compound 3a:

[0403] 1HNMR(400MHz, CDCl3)δ7.97–7.84(m,4H),7.83(dd,J=8.4,2.0Hz,1H),7.63(dd, J=8.3,2.5Hz,1H),7.48–7.37(m,3H),7.32–7.17(m,5H),6.96(dd,J=8.4,2.1Hz ,1H),6.80(dd,J=7.3,3.3Hz,1H),5.70(ddt,J=8.3,5.4,2.9Hz,1H),3.14–2.99 (m,1H),2.98–2.76(m,2H),2.64(dt,J=14.2,3.4Hz,1H),0.89(d,J=3.4Hz,3H);

[0404] 13 CNMR (101MHz, CDCl3) δ142.69 (d, J = 18.8Hz), 140.85 (d, J = 47.3Hz), 135.47 (d, J = 16.5Hz) ,133.83,133.29,133.09,133.00,132.58,132.35,132.19,131.55,130.22,129.73,129. 03,128.74,128.40,128.36,127.77,127.60,126.85,126.79,126.16,126.03,125.32,12 5.23, 125.11 (d, J = 9.7Hz), 31.71 (d, J = 20.0Hz), 30.34 (d, J = 14.9Hz), 2.94 (d, J = 10.7Hz);

[0405] 31 PNMR (162MHz,CDCl3)δ-5.27.

[0406] Example 8: Preparation of (4R,11bS)-4-(2-((R)-(4-Methoxyphenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5a)

[0407]

[0408] Referring to Experimental Procedure D, 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 ml). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere; and stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and cooled to -116 °C; MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 hour. p-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, which took 10 to 12 hours; it was concentrated to obtain a crude reaction mixture; tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5a in the crude reaction mixture had an 83% yield and 11:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere; then stirred at room temperature for 12 hours, concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5a·BH3, and then compound 5a·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5a (313.5 mg, in the form of white foam, 58% yield, >99% de). The obtained compound 5a was taken to measure specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0409] Characterization of compound 5a:

[0410]

[0411] 1HNMR(600MHz,CDCl3)δ7.93–7.87(m,3H),7.76(d,J=8.3Hz,1H),7.64(dt,J=7.4,1.9Hz,1H),7.54(d,J=8.3Hz,1H),7.54–7.48(m,2H),7.40(m,2H),7.31(m,1H),7.27–7.19(m,2H),7.21–7.11(m,3H),6.90–6.86(m,2H),6.85(d,J=8.3Hz,1H),6.79–6.76(m,1H),5.20(dt,J=7.4,3.7Hz,1H),3.77(s,3H),2.98(dd,J=11.9,2.1Hz,1H),2.71(dd,J=17.3,11.9Hz,1H),2.63(dd,J=14.4,12.1Hz,1H),2.22(dd,J=14.4,3.7Hz,1H),0.76(dd,J=3.8,1.7Hz,3H);

[0412] 13 CNMR(151MHz,CDCl3)δ160.68,143.70(d,J=30.6Hz),143.47(d,J=5.5Hz),136.81,136.80,136.66(d,J=15.0Hz),134.56,133.75,133.70(d,J=4.8Hz),133.09,132.87,132.44,132.32(d,J=1.9Hz),132.16,131.66(d,J=2.1Hz),129.15,129.09,128.98,128.46,128.35,128.31,127.80(d,J=2.3Hz),127.50,126.82,126.80,126.00,125.98,125.12,125.00,113.77,55.15,31.69(d,J=22.4Hz),30.77(d,J=16.9Hz),-3.01(d,J=12.5Hz);

[0413] 31 PNMR(162MHz,CDCl3)δ-3.07;

[0414] HRMS(ESI)m / zcalcdforC 36 H 32 OPSi[M+H] + 539.1955,found539.1953.

[0415] Example 9: Preparation of (4R,11bS)-4-(2-((R)-(4-Fluorophenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5b)

[0416]

[0417] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere; and stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 hour. p-FC6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, which took 10 to 12 hours to warm to room temperature; it was concentrated to obtain a crude reaction mixture; tetrachloroethane was used as an internal standard to detect the crude reaction mixture. 1 H NMR and 31 PNMR determined that compound 5b in the crude reaction mixture had an 87% yield and 12:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere; stirred at room temperature for 12 hours, concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5b·BH3, and then compound 5b·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5b (in the form of white foam, 342.9 mg, 65% yield, >99% de). The obtained compound 5b was taken to measure specific rotation, hydrogen spectrum, carbon spectrum, 19 FNMR, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0418] Characterization of compound 5b:

[0419]

[0420] 1H NMR(600MHz,CDCl3)δ7.95–7.88(m,3H),7.78(d,J=8.3Hz,1H),7.63(d,J=7.4Hz,1H),7.59–7.53(m,2H),7.52(d,J=8.3Hz,1H),7.46–7.38(m,2H),7.34(t,J=7.4Hz,1H),7.28–7.13(m,5H),7.03(t,J=8.8Hz,2H),6.86(d,J=8.3Hz,1H),6.79(dd,J=7.7,2.7Hz,1H),5.21(m,1H),2.98(dd,J=11.9,2.4Hz,1H),2.74–2.60(m,2H),2.20(dd,J=14.4,3.7Hz,1H),0.77(dd,J=3.8,1.5Hz,3H);

[0421] 13 C NMR(151MHz,CDCl3)δ163.89(d,J=248.5Hz),143.59(d,J=21.8Hz),142.94(d,J=47.4Hz),137.29(d,J=2.6Hz),137.24(d,J=2.6Hz),136.61(d,J=15.2Hz),134.38,133.70(d,J=4.7Hz),133.57,133.14,132.90(d,J=1.3Hz),132.48,132.37(d,J=3.8Hz),132.33(d,J=2.3Hz),132.17,131.82(d,J=2.2Hz),129.40,129.13,129.05,128.53,128.36,128.32,127.71(d,J=2.4Hz),127.56,126.84,126.79,126.06,126.03,125.18,125.07,115.22,115.09,31.59,30.76(d,J=16.5Hz),-3.08(d,J=12.5Hz);

[0422] 19 F NMR(377MHz,CDCl3)δ-111.56;

[0423] 31 P NMR(243MHz,CDCl3)δ-3.30;

[0424] HRMS(ESI)m / z calcd for C 35 H 29FPSi[M+H] + 527.1755, found 527.1755.

[0425] Example 10: Preparation of (4R,11bS)-4-(2-((R)-Methyl(4-(trifluoromethyl)phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5c)

[0426]

[0427] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. p-CF3-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 H NMR and 31 P NMR analysis determined that compound 5c in the crude reaction mixture had an 82% yield and 20:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere; stirred for 12 hours at room temperature; concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5c·BH3, and then compound 5c·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5c (in the form of white foam, 356.4 mg, 62% yield, >99% de). The obtained compound 5c was measured for specific rotation, hydrogen spectrum, carbon spectrum, 19 FNMR, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0428]

[0429] 1 HNMR(600MHz,CDCl3)δ7.93(d,J=8.1Hz,1H),7.90(dd,J=8.4,3.8Hz,2H),7.80(d,J=8.3Hz,1H),7.70(d,J=7.7Hz,2H),7.62(m,1H),7.58(d,J=7.8Hz,2H),7.47(d,J=8.3Hz,1H),7.45–7.38(m,2H),7.36(t,J=7.4Hz,1H),7.24(d,J=6.2Hz,2H),7.21–7.17(m,2H),7.15(d,J=8.5Hz,1H),6.90(d,J=8.3Hz,1H),6.82(dd,J=7.7,2.6Hz,1H),5.29–5.24(m,1H),2.97(dd,J=11.9,2.7Hz,1H),2.68(dt,J=17.2,11.7Hz,2H),2.29(dd,J=14.4,3.6Hz,1H),0.79(dd,J=3.8,1.6Hz,3H);

[0430] 13 CNMR(151MHz,CDCl3)δ143.82(d,J=21.5Hz),142.22(d,J=4.5Hz),142.01(d,J=48.1Hz),136.56(d,J=15.2Hz),135.54,135.52,134.21,133.67(d,J=4.8Hz),133.46,133.21,132.92(d,J=1.5Hz),132.51,132.33(d,J=2.1Hz),131.99(d,J=2.1Hz),131.99,131.19(q,J=32.1Hz),129.68,129.30,129.05,128.59,128.37,128.33,127.63,126.85,126.80,126.09,126.07,125.22,125.13,124.43(q,J=3.7Hz),31.66(d,J=21.9Hz),30.91(d,J=16.3Hz),-3.30(d,J=12.2Hz);

[0431] 19 FNMR(377MHz,CDCl3)δ-62.83;

[0432] 31PNMR (243MHz,CDCl3)δ-3.36;

[0433] HRMS (ESI) m / zcalcdforC 36 H 29 F3PSi[M+H] + 577.1723, found 577.1722.

[0434] Example 11: Preparation of (4S,11bR)-4-(2-((R)-Methyl(naphthalen-2-yl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5d)

[0435]

[0436] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. Naphthalene-2-ylmagnesium bromide (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31PNMR analysis determined that compound 5d in the crude reaction mixture had an 81% yield and a 9:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere, stirred at room temperature for 12 hours, concentrated, and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5d·BH3, and then compound 5d·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5d (as a white solid, 346.9 mg, 62% yield, >99% de). The obtained compound 5d was taken to measure the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0437] Characterization of compound 5d:

[0438]

[0439] 1 HNMR (400MHz, CDCl3) δ8.09(s,1H),7.92(d,J=8.2Hz,1H),7.88(d,J=8.2Hz,1H),7.84(d,J=8.3Hz,1H) ,7.82–7.76(m,4H),7.70–7.63(m,2H),7.48–7.32(m,6H),7.22(d,J=3.8Hz,2H),7.20–7.14(m,2H),7.1 1(d,J=8.5Hz,1H),6.89(d,J=8.4Hz,1H),6.82(dd,J=7.7,2.7Hz,1H),5.36(dq,J=7.3,3.7Hz,1H),2.9 5(dd,J=11.8,2.5Hz,1H),2.71–2.58(m,2H),2.27(dd,J=14.3,3.7Hz,1H),0.85(dd,J=3.8,1.6Hz,3H);

[0440] 13CNMR(101MHz, CDCl3)δ143.85(d,J=21.9Hz),143.13(d,J=47.7Hz),136.71(d,J=15.2Hz),136.16,136.14,134.43(d,J=4.0Hz ),134.41,133.91,133.69,133.62(d,J=4.9Hz),133.14,133.12,132.86,132.45,132.29(d,J=2.0Hz),132.18,131.86(d,J=1. 8Hz),131.35,131.32,129.36,129.12,128.47(d,J=1.3Hz),128.33,128.30,128.23,127.89,127.71(d,J=2.1Hz),127.54,127 .15,126.83,126.77,126.60,126.07,125.98,125.10,125.03,31.67(d,J=22.6Hz),30.98(d,J=16.8Hz),-3.06(d,J=12.2Hz);

[0441] 31 PNMR (162MHz,CDCl3)δ-3.10;

[0442] HRMS (ESI) m / zcalcdforC 39 H 32 PSi[M+H] + 559.2005,found 559.2004.

[0443] Example 12: Preparation of (4R,11bS)-4-(2-((R)-Methyl(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5e)

[0444]

[0445] Referring to Experimental Procedure D, 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL), the reaction mixture was cooled to -84 °C, n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. PhMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5e in the crude reaction mixture had a 77% yield and 8:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere, and then stirred at room temperature for 12 hours; concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain 5e·BH3, and then compound 5e·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5e (white foam, 278.8 mg, 55% yield, >99% de). The obtained compound 5e was taken to measure specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0446] Characterization of compound 5e:

[0447]

[0448] 1HNMR(400MHz,CDCl3)δ7.96–7.85(m,3H),7.78(d,J=8.3Hz,1H),7.65(dt,J=7.4,1.9Hz,1H),7.58(m,2H),7.51(dd,J=8.3,1.1Hz,1H),7.45–7.38(m,2H),7.37–7.29(m,4H),7.28–7.20(m,2H),7.20–7.11(m,3H),6.87(d,J=8.3Hz,1H),6.79(dd,J=7.8,2.8Hz,1H),5.22(m,1H),2.97(dd,J=11.8,2.3Hz,1H),2.75–2.57(m,2H),2.20(dd,J=14.3,3.8Hz,1H),0.78(dd,J=3.8,1.7Hz,3H);

[0449] 13 CNMR(151MHz,CDCl3)δ143.67(d,J=21.9Hz),143.24(d,J=47.7Hz),136.90(d,J=4.2Hz),136.71(d,J=15.0Hz),135.32,135.31,134.50,133.73,133.68(d,J=4.6Hz),133.13,132.88,132.46,132.32(d,J=2.0Hz),132.18,131.76(d,J=2.2Hz),129.31,129.27,129.09,129.05,128.49(d,J=1.5Hz),128.36,128.32,127.97,127.77(d,J=2.2Hz),127.53,126.84,126.79,125.99,125.12,125.02,31.59(d,J=22.4Hz),30.86(d,J=16.8Hz),-3.22(d,J=12.6Hz);

[0450] 31 PNMR(162MHz,CDCl3)δ-3.03;

[0451] HRMS(ESI)m / zcalcdforC 35 H 30 PSi[M+H] + 509.1849,found509.1848.

[0452] Example 13: Preparation of (4S,11bR)-4-(2-((S)-Methyl(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5f)

[0453]

[0454] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. MeMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5f in the crude reaction mixture had a 78% yield and 1:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere, and then stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to give compound 5f·BH3 and compound 5e·BH3, respectively, and then compound 5f·BH3 and compound 5e·BH3 were mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to give a crude product of compound 5f and a crude product of compound 5e. The crude products of compound 5f·BH3 and compound 5e·BH3 were concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5f (white foam, 161.3 mg, 32% yield, >99% de) and compound 5e (white foam, 142.1 mg, 28% yield, >99% de). The obtained compounds 5f and 5e were measured for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0455] Characterization of compound 5f:

[0456]

[0457] 1 HNMR(600MHz,CDCl3)δ7.95–7.87(m,3H),7.77(d,J=8.3Hz,1H),7.64–7.56(m,3H),7.50(d,J=8.3Hz,1H),7.45–7.34(m,5H),7.32(t,J=7.6Hz,1H),7.23(d,J=9.1Hz,2H),7.17(dt,J=18.7,8.1Hz,3H),6.86(d,J=8.3Hz,1H),6.81(dd,J=7.7,2.8Hz,1H),5.30(dt,J=7.2,3.8Hz,1H),2.95(dd,J=11.8,2.3Hz,1H),2.67(dd,J=16.2,12.2Hz,2H),2.30(dd,J=14.4,3.7Hz,1H),0.73(d,J=3.7Hz,3H);

[0458] 13 CNMR(151MHz,CDCl3)δ143.73(d,J=22.0Hz),142.98(d,J=46.8Hz),136.93(d,J=3.9Hz),136.40,136.31,135.36,134.45,133.75,133.67(d,J=4.9Hz),133.13,132.88,132.45,132.31,132.16,131.66,129.37,129.26,129.01,128.97,128.48,128.35,128.31,128.03,127.75(d,J=1.6Hz),127.54,126.83,126.78,125.99,125.12,125.02,31.60(d,J=22.4Hz),30.77(d,J=16.9Hz),-3.01(d,J=11.6Hz);

[0459] 31 PNMR(243MHz,CDCl3)δ-3.34;

[0460] HRMS(ESI)m / zcalcdforC 35 H 30 PSi[M+H] + 509.1849,found509.1850.

[0461] Characterization of Compound 5e:

[0462]

[0463] 1 HNMR(400MHz,CDCl3)δ7.96–7.85(m,3H),7.78(d,J=8.3Hz,1H),7.65(dt,J=7.4,1.9Hz,1H),7.58(m,2H),7.51(dd,J=8.3,1.1Hz,1H),7.45–7.38(m,2H),7.37–7.29(m,4H),7.28–7.20(m,2H),7.20–7.11(m,3H),6.87(d,J=8.3Hz,1H),6.79(dd,J=7.8,2.8Hz,1H),5.22(m,1H),2.97(dd,J=11.8,2.3Hz,1H),2.75–2.57(m,2H),2.20(dd,J=14.3,3.8Hz,1H),0.78(dd,J=3.8,1.7Hz,3H);

[0464] 13 CNMR(151MHz,CDCl3)δ143.67(d,J=21.9Hz),143.24(d,J=47.7Hz),136.90(d,J=4.2Hz),136.71(d,J=15.0Hz),135.32,135.31,134.50,133.73,133.68(d,J=4.6Hz),133.13,132.88,132.46,132.32(d,J=2.0Hz),132.18,131.76(d,J=2.2Hz),129.31,129.27,129.09,129.05,128.49(d,J=1.5Hz),128.36,128.32,127.97,127.77(d,J=2.2Hz),127.53,126.84,126.79,125.99,125.12,125.02,31.59(d,J=22.4Hz),30.86(d,J=16.8Hz),-3.22(d,J=12.6Hz);

[0465] 31 PNMR(162MHz,CDCl3)δ-3.03;

[0466] HRMS(ESI)m / zcalcdforC 35 H 30 PSi[M+H] +509.1849, found 509.1848.

[0467] Example 14: Preparation of (4R,11bS)-4-(2-((R)-Mesityl(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5g)

[0468]

[0469] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C; MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. Isopropylmagnesium bromide (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5g in the crude reaction mixture had a yield of 72% and >99:1dr. The crude reaction mixture was then concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5g (white foam, 359.6 mg, 65% yield, >99% de). The obtained compound 5g was measured for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0470] Characterization of compound 5g:

[0471]

[0472] 1HNMR(400MHz, CDCl3)δ7.88(m,4H),7.64(dt,J=7.5,1.8Hz,1H),7.45–7.35 (m,2H),7.32(td,J=7.4,1.3Hz,1H),7.26–7.07(m,7H),7.01(dd,J=7.7,2.5 Hz, 1H), 6.86 (s, 2H), 5.45 (dq, J=8.4, 4.2Hz, 1H), 2.78 (ddd, J=13.0, 9.2, 6. 2Hz,2H),2.56(dd,J=14.5,3.2Hz,1H),2.32(m,10H),0.69(d,J=4.1Hz,3H);

[0473] 13 CNMR(151MHz, CDCl3)δ144.82,144.80(d,J=22.3Hz),144.52(d,J=47.9Hz),139.34,135.68,135.5 8,134.68,134.14,133.38,133.36,132.78,132.43,132.32,131.59,131.57,131.49(d,J=4.7Hz),1 29.27,129.07,128.84,128.30,128.26,127.69,127.67,127.66,126.89,126.83,125.99,125.90,1 25.04,125.03,31.84(d,J=16.5Hz),31.47(d,J=23.3Hz),24.03,24.01,21.33,-2.33(d,J=9.1Hz).

[0474] 31 PNMR (162MHz,CDCl3)δ-2.44;

[0475] HRMS (ESI) m / zcalcdforC 38 H 36 PSi[M+H] + 551.2318, found 551.2317.

[0476] Example 15: Preparation of (4S,11bR)-4-(2-((S)-Isopropyl(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5h)

[0477]

[0478] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. i-PrMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5h in the crude reaction mixture had a 75% yield and 4:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain 5h·BH3, and then compound 5h·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5h (white foam, 218.9 mg, 41% yield, >99% de). The obtained compound 5h was taken to measure the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0479]

[0480] 1HNMR(400MHz,CDCl3)δ7.90(dd,J=8.2,3.1Hz,3H),7.75(d,J=8.3Hz,1H),7.72(dt,J=7.4,1.9Hz,1H),7.65–7.59(m,2H),7.50(dd,J=8.4,1.2Hz,1H),7.44–7.31(m,6H),7.24–7.11(m,5H),6.86–6.79(m,2H),5.01(dd,J=7.3,4.5Hz,1H),2.91(dd,J=11.8,2.2Hz,1H),2.69–2.58(m,2H),2.25(dd,J=14.3,3.7Hz,1H),1.72(m,1H),1.12(dd,J=7.4,3.8Hz,6H);

[0481] 13 CNMR(151MHz,CDCl3)δ144.03(d,J=22.0Hz),141.96(d,J=47.8Hz),136.78,136.68,136.00,135.99,135.76(d,J=3.2Hz),134.50,133.82,133.67(d,J=4.5Hz),133.11,132.88,132.44,132.32,132.16,131.73,129.31,129.18,128.94,128.84,128.47,128.36,128.30,127.95,127.74(d,J=1.5Hz),127.55,126.83,126.78,126.00,125.97,125.12,125.00,31.56(d,J=22.1Hz),30.96(d,J=17.3Hz),19.24,19.02,12.58(d,J=9.8Hz);

[0482] 31 PNMR(162MHz,CDCl3)δ-2.46;

[0483] HRMS(ESI)m / zcalcdforC 37 H 34 PSi[M+H] + 537.2162,found537.2162.

[0484] Example 16: Preparation of (4R,11bS)-4-(2-((S)-Cyclohexyl(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5i)

[0485]

[0486] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. CyMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5i in the crude reaction mixture had a 75% yield and 12:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain 5i·BH3, and then compound 5i·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5i (white foam, 324.7 mg, 56% yield, >99% de). The obtained compound 5i was taken to measure the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0487] Characterization of compound 5i:

[0488]

[0489] 1HNMR(600MHz,CDCl3)δ7.90(dd,J=8.3,3.0Hz,3H),7.76(d,J=8.3Hz,1H),7.71(d,J=7.4Hz,1H),7.62(dd,J=6.7,2.8Hz,2H),7.49(d,J=8.3Hz,1H),7.41(m,2H),7.35(m,4H),7.27–7.21(m,2H),7.21–7.11(m,3H),6.83(dd,J=8.4,3.5Hz,2H),5.00(dd,J=6.9,4.7Hz,1H),2.90(dd,J=11.9,2.3Hz,1H),2.65(ddd,J=19.5,15.6,12.1Hz,2H),2.28(dd,J=14.4,3.7Hz,1H),1.78(dd,J=24.3,12.1Hz,2H),1.74–1.65(m,3H),1.62–1.53(m,1H),1.37–1.19(m,5H);

[0490] 13 CNMR(151MHz,CDCl3)δ144.11(d,J=22.3Hz),141.75(d,J=47.0Hz),136.87(d,J=14.6Hz),136.06(d,J=2.6Hz),135.65(d,J=3.3Hz),134.52,133.85,133.67(d,J=4.8Hz),133.11,132.88,132.44,132.33,132.16,131.72,129.28,129.16,128.94,128.83,128.48,128.36,128.31,127.93,127.75(d,J=2.3Hz),127.57,126.84,126.78,126.01,125.97,125.12,125.00,31.60(d,J=22.8Hz),31.04(d,J=17.2Hz),29.17,28.99,28.09,28.00,26.97,24.29(d,J=9.6Hz);

[0491] 31 PNMR(243MHz,CDCl3)δ-2.27;

[0492] HRMS(ESI)m / zcalcdforC 40 H 38 PSi[M+H] + 577.2475,found577.2472.

[0493] Example 17: Preparation of (4R,11bS)-4-(2-((S)-Cyclohexyl(4-fluorophenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5j)

[0494]

[0495] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. p-FC6H4SiHCl2 (390.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. CyMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5j in the crude reaction mixture had a 78% yield and 22:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5j·BH3, and then compound 5j·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5j (in the form of white foam, 340.8 mg, 57% yield, >99% de). The obtained compound 5j was taken to measure specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0496] Characterization of compound 5j:

[0497]

[0498] 1 HNMR(400MHz,CDCl3)δ7.91(dd,J=8.2,2.6Hz,3H),7.77(d,J=8.3Hz,1H),7.69(dt,J=7.5,1.8Hz,1H),7.61(dd,J=8.4,6.2Hz,2H),7.50(d,J=8.3Hz,1H),7.46–7.38(m,2H),7.35(t,J=7.4Hz,1H),7.28–7.12(m,5H),7.06(dd,J=10.0,7.7Hz,2H),6.89–6.79(m,2H),4.97(dd,J=7.1,4.6Hz,1H),2.92(dd,J=11.7,2.3Hz,1H),2.66(ddd,J=24.5,15.6,12.1Hz,2H),2.27(dd,J=14.3,3.7Hz,1H),1.73(m,5H),1.57(m,1H),1.43–1.19(m,5H);

[0499] 13 CNMR(151MHz,CDCl3)δ163.89(d,J=248.8Hz),143.99(d,J=21.9Hz),141.61(d,J=47.9Hz),138.02(d,J=3.0Hz),137.97(d,J=2.9Hz),136.84(d,J=14.8Hz),134.38,133.67(d,J=5.0Hz),133.65,133.14,132.89(d,J=1.5Hz),132.46,132.33(d,J=2.1Hz),132.17,131.87,131.09(t,J=3.5Hz),129.29,128.98,128.94,128.54,128.37,128.31,127.65(d,J=2.3Hz),127.60,126.83,126.77,126.07,126.02,125.18,125.06,115.17,115.04,31.63(d,J=22.6Hz),31.06(d,J=16.8Hz),29.12,28.92,28.03,27.95,26.93,24.42(d,J=9.8Hz);

[0500] 19 FNMR(377MHz,CDCl3)δ-111.54;

[0501] 31 PNMR(162MHz,CDCl3)δ-2.68;

[0502] HRMS (ESI) m / zcalcdforC 40 H 37 FPSi[M+H] + 595.2381, found 595.2376.

[0503] Example 18: Preparation of (4R,11bS)-4-(2-((S)-Cyclohexyl(4-methoxyphenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5k)

[0504]

[0505] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. p-MeO-C6H4SiHCl2 (414.3 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. CyMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5k in the crude reaction mixture had a 72% yield and 17:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5k·BH3, and then compound 5k·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5k (in the form of white foam, 368.9 mg, 61% yield, >99% de). The specific rotation, hydrogen spectrum, carbon spectrum,31 PNMR and mass spectrometry, etc., the results are as follows:

[0506] Characterization of compound 5k:

[0507]

[0508] 1 HNMR(400MHz, CDCl3)δ7.91(d,J=7.9Hz,3H),7.75(d,J=8.4Hz,1H),7.70(dt,J=7.5,1.9Hz,1H), 7.62–7.50(m,3H),7.46–7.37(m,2H),7.33(t,J=7.4Hz,1H),7.29–7.09(m,5H),6.91(d,J=6.7Hz, 2H),6.86–6.76(m,2H),4.99(dd,J=6.9,4.5Hz,1H),3.80(s,3H),2.91(dd,J=11.7,2.0Hz,1H),2. 76–2.59(m,2H),2.30(dd,J=14.3,3.8Hz,1H),1.85–1.64(m,5H),1.53(m,1H),1.35–1.20(m,5H);

[0509] 13 CNMR(101MHz, CDCl3)δ160.66,144.01(d,J=22.2Hz),142.05(d,J=46.5Hz),137.55,137.52,136.76(d,J=14.4Hz),134.58,133 .89,133.71(d,J=4.9Hz),133.09,132.88(d,J=1.0Hz),132.44,132.33(d,J=1.8Hz),132.15,131.63(d,J=1.0Hz),129.04,128. 95,128.76,128.46,128.36,128.31,127.77(d,J=1.0Hz),127.54,126.81(d,J=3.3Hz),126.18(d,J=3.0Hz),126.01,125.97,12 5.12,124.99,113.74,55.15,31.68(d,J=22.8Hz),30.98(d,J=17.2Hz),29.18,28.94,28.10,28.03,26.99,24.50(d,J=9.0Hz);

[0510] 31 PNMR (162MHz,CDCl3)δ-2.41;

[0511] HRMS (ESI) m / zcalcdforC 41 H 40 OPSi[M+H] + 607.2581, found 607.2575.

[0512] Example 19: Preparation of (4R,11bS)-4-(2-((R)-Cyclohexyl(4-methoxyphenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 51)

[0513]

[0514] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. CySiHCl2 (366.3 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. p-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that the crude reaction mixture had a 89% yield and 5:1 dr of compound 5l. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain 5l·BH3, and then compound 5I·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5l (white foam, 262.1 mg, 43% yield, >99% de). The specific rotation, hydrogen spectrum, carbon spectrum, 31PNMR and mass spectrometry, etc., the results are as follows:

[0515] Characterization of compound 5l:

[0516]

[0517] 1 HNMR(400MHz, CDCl3)δ7.91(d,J=8.2Hz,3H),7.79–7.70(m,2H),7.58–7.50(m,3H),7.46–7.38 (m,2H),7.33(m,1H),7.25–7.21(m,2H),7.21–7.10(m,3H),6.87–6.79(m,3H),6.76(m,1H),4.8 6(dd,J=6.5,4.4Hz,1H),3.75(s,3H),2.96(dd,J=11.8,2.0Hz,1H),2.64(ddd,J=26.2,15.7,11 .8Hz,2H),2.14(dd,J=14.3,3.6Hz,1H),1.86(d,J=8.5Hz,1H),1.73(m,5H),1.41–1.21(m,6H);

[0518] 13 CNMR (151MHz, CDCl3) δ160.56, 143.47 (d, J = 21.4Hz), 142.72 (d, J = 49.0Hz), 137.47, 137.45, 137.28 (d, J = 15.2Hz), 134.6 4,133.84,133.73(d,J=4.5Hz),133.05,132.88(d,J=1.5Hz),132.44,132.35(d,J=2.3Hz),132.16,131.57,129.09,129.0 1,128.91,128.47,128.36,128.32,127.81(d,J=2.3Hz),127.50,126.83,126.12(d,J=3.4Hz),126.01,125.96,125.13,1 24.98,113.69,54.43,31.74(d,J=22.5Hz),31.03(d,J=16.9Hz),29.20,29.17,28.21,28.02,27.04,24.15(d,J=10.5Hz);

[0519] 31 PNMR (162MHz,CDCl3)δ-1.51;

[0520] HRMS (ESI) m / zcalcdforC 41 H 40 OPSi[M+H] + 607.2581, found 607.2578.

[0521] Example 20: Preparation of (4S,11bR)-4-(2-((R)-(2-Isopropoxyphenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5m)

[0522]

[0523] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. o-iPrO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5m in the crude reaction mixture had a 90% yield and 26:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5m·BH3, and then compound 5m·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5m (white solid, 397.9 mg, 70% yield, >99% de). The obtained compound 5m was taken to measure specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0524] Characterization of Compound 5m:

[0525]

[0526] 1 HNMR(600MHz,CDCl3)δ7.96–7.83(m,3H),7.78(d,J=8.3Hz,1H),7.72(dt,J=7.5,1.8Hz,1H),7.51(dd,J=7.2,1.8Hz,1H),7.44(d,J=8.3Hz,1H),7.43–7.33(m,2H),7.30(td,J=7.6,2.1Hz,2H),7.26–7.08(m,5H),6.91(dd,J=7.9,5.9Hz,2H),6.82(dd,J=7.6,2.5Hz,1H),6.76(d,J=8.3Hz,1H),5.20(dq,J=7.4,3.8Hz,1H),4.50(h,J=6.0Hz,1H),2.90(dd,J=11.8,1.9Hz,1H),2.60(ddd,J=40.2,15.6,12.1Hz,2H),2.31(dd,J=14.4,3.5Hz,1H),1.10(dd,J=12.2,6.0Hz,6H),0.74(d,J=3.7Hz,3H);

[0527] 13 CNMR(151MHz,CDCl3)δ162.45,143.90(d,J=45.9Hz),143.61(d,J=22.8Hz),137.63(d,J=3.6Hz),136.74(d,J=14.5Hz),134.72,134.08,133.56(d,J=4.6Hz),133.14,132.81,132.39,132.30,132.19,131.21,131.17,129.11,128.75,128.55,128.37,128.33,128.28,127.84,127.49,126.84,126.78,125.92,125.91,125.62(d,J=3.5Hz),125.02,124.95,120.31,110.98,69.00,31.68(d,J=22.9Hz),31.10(d,J=17.0Hz),21.98,21.83,-3.39(d,J=11.0Hz);

[0528] 31PNMR (243MHz,CDCl3)δ-3.16;

[0529] HRMS (ESI) m / zcalcdforC 38 H 36 OPSi[M+H] + 567.2268, found 567.2265.

[0530] Example 21: Preparation of (4S,11bR)-4-(2-((R)-Methyl(2-phenoxyphenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5n)

[0531]

[0532] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. o-PhO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31PNMR analysis determined that compound 5n in the crude reaction mixture had a 47% yield and 7:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5n·BH3, and then compound 5n·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5n (white solid, 197.1 mg, 33% yield, >99% de). The obtained compound 5n was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0533] Characterization of compound 5n:

[0534]

[0535] 1 HNMR (600MHz, CDCl3) δ7.94–7.84(m,3H),7.78(d,J=8.3Hz,1H),7.64(d,J=7.4Hz,1H),7.56(dd,J=7.4,1.7Hz,1H), 7.46(d,J=8.3Hz,1H),7.43–7.34(m,2H),7.29(td,J=7.8,1.7Hz,1H),7.20(ddd,J=30.9,22.3,7.2Hz,7H),7.08(dt, J=14.1,7.4Hz,2H),7.00(t,J=7.4Hz,1H),6.92(d,J=8.4Hz,1H),6.88–6.68(m,4H),5.29(dq,J=7.5,3.8Hz,1H),2.9 4(dd,J=11.9,2.0Hz,1H),2.65(ddd,J=37.1,15.7,12.0Hz,2H),2.36(dd,J=14.4,3.5Hz,1H),0.75(d,J=3.7Hz,3H);

[0536] 13CNMR (151MHz, CDCl3) δ162.05, 157.25, 143.50 (d, J = 22.5Hz), 142.77 (d, J = 46.1Hz), 137.59 (d, J = 3.1Hz), 136.61, 13 6.51,134.60,133.87,133.64(d,J=5.1Hz),133.12,132.84,132.43,132.31(d,J=1.5Hz),132.18,131.39,131.31,1 29.63,129.12,129.00,128.83,128.42,128.33,128.30,127.97(d,J=3.9Hz),127.76,127.53,126.82,126.79,125. 97,125.08,125.00,123.29,123.05,118.94,117.47,31.77(d,J=22.8Hz),30.94(d,J=16.9Hz),-3.32(d,J=11.0Hz);

[0537] 31 PNMR (243MHz,CDCl3)δ-3.48;

[0538] HRMS (ESI) m / zcalcdforC 41 H 34 OPSi[M+H] + 601.2111, found 601.2109.

[0539] Example 22: Preparation of (4S,11bR)-4-(2-((R)-(2,6-Dimethoxyphenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5o)

[0540]

[0541] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. 2,6-di-MeO-C6H3PhMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5o in the crude reaction mixture had a 91% yield and 12:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5o·BH3, and then compound 5o·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5o (white solid, 314.5 mg, 55% yield, >99% de). The obtained compound 5o was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0542] Characterization of compound 5o:

[0543]

[0544] 1HNMR(600MHz,CDCl3)δ7.93–7.81(m,3H),7.79(d,J=8.3Hz,1H),7.58(dt,J=7.5,1.9Hz,1H),7.44–7.33(m,3H),7.31(t,J=8.2Hz,1H),7.27–7.22(m,2H),7.21–7.11(m,3H),7.07(td,J=7.5,1.5Hz,1H),7.01(d,J=8.3Hz,1H),6.85(dd,J=7.7,2.5Hz,1H),6.50(d,J=8.2Hz,2H),5.40(dq,J=7.6,3.9Hz,1H),3.59(s,6H),2.88(dd,J=11.7,1.9Hz,1H),2.76(dd,J=14.5,12.6Hz,1H),2.59–2.46(m,2H),0.71(d,J=3.9Hz,3H);

[0545] 13 CNMR(151MHz,CDCl3)δ165.47,145.06(d,J=46.8Hz),143.38(d,J=22.1Hz),135.80,135.70,134.87,134.20,133.51(d,J=5.1Hz),133.16,132.76,132.37,132.29,132.28,132.21,131.03,129.23,128.44,128.32,128.29,128.25,127.79,127.78,127.50,126.79,125.90,125.88,124.97,124.92,112.59(d,J=4.9Hz),104.12,55.67,31.73(d,J=23.8Hz),31.46(d,J=17.4Hz),-1.98,-2.01(d,J=9.8Hz);

[0546] 31 PNMR(243MHz,CDCl3)δ-3.10;

[0547] HRMS(ESI)m / zcalcdforC 37 H 34 O2PSi[M+H] + 569.2060,found569.2058.

[0548] Example 23: Preparation of (4S,11bR)-4-(2-((R)-(2-Methoxynaphthalen-1-yl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5p)

[0549]

[0550] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. (2-Methoxynaphthalen-1-yl)magnesium bromide (3.5 mmol, 3.5 equiv) was then added and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5p in the crude reaction mixture had a 93% yield and 28:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5p·BH3, and then compound 5p·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5p (white solid, 431.5 mg, 73% yield, >99% de). The obtained compound 5p was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0551] Characterization of compound 5p:

[0552]

[0553] 1HNMR(400MHz,CDCl3)δ8.55–8.37(m,1H),7.92(d,J=8.9Hz,1H),7.90–7.85(m,2H),7.81(dd,J=10.5,8.2Hz,2H),7.71(dt,J=7.6,1.7Hz,1H),7.60(d,J=8.3Hz,1H),7.46–7.27(m,5H),7.20–6.98(m,8H),6.39(dt,J=8.4,1.3Hz,1H),5.89(dq,J=7.6,3.8,2.9Hz,1H),3.48(d,J=1.0Hz,3H),2.79(dd,J=14.4,12.7Hz,1H),2.74–2.53(m,2H),1.92(dd,J=15.7,11.5Hz,1H),0.77(dd,J=3.9,1.5Hz,3H);

[0554] 13 CNMR(101MHz,CDCl3)δ163.42,144.70(d,J=25.4Hz),144.35,138.05,135.77,135.62,134.48,134.20,133.34,133.08(d,J=5.1Hz),132.65(d,J=1.3Hz),132.55,132.36,132.26,132.14(d,J=2.2Hz),131.30(d,J=2.5Hz),129.76,129.28,128.75,128.66,128.54,128.20,128.12,128.11,127.63,127.39(d,J=2.4Hz),126.83,126.77,126.73,125.91,125.77,124.98,124.89,123.70,119.60(d,J=4.3Hz),113.64,56.25,31.96(d,J=16.8Hz),31.53(d,J=23.7Hz),-2.91,-3.01;

[0555] 31 PNMR(162MHz,CDCl3)δ-3.26;

[0556] HRMS(ESI)m / zcalcdforC 40 H 34 OPSi[M+H] + 589.2111,found589.2108.

[0557] Example 24: Preparation of (4R,11bS)-4-(2-((R)-(2-Methoxyphenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5q)

[0558]

[0559] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. o-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5q in the crude reaction mixture had an 81% yield and 21:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5q·BH3, and then compound 5q·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5q (in the form of white foam, 314.1 mg, 58% yield, >99% de). The obtained compound 5q was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0560] Characterization of compound 5q:

[0561]

[0562] 1HNMR(600MHz,CDCl3)δ7.92(d,J=8.2Hz,1H),7.88(t,J=9.3Hz,2H),7.78(d,J=8.3Hz,1H),7.63(d,J=7.5Hz,1H),7.49(d,J=8.3Hz,1H),7.45–7.33(m,4H),7.31(t,J=7.4Hz,1H),7.28–7.10(m,5H),6.94(t,J=7.3Hz,1H),6.90(d,J=8.3Hz,1H),6.82(t,J=8.4Hz,2H),5.26(dq,J=7.4,3.8Hz,1H),3.71(s,3H),2.95(dd,J=11.9,2.0Hz,1H),2.68(ddd,J=17.7,12.1,4.7Hz,2H),2.37(dd,J=14.4,3.6Hz,1H),0.73(d,J=2.5Hz,2H);

[0563] 13 CNMR(151MHz,CDCl3)δ164.40,143.52(d,J=13.6Hz),143.29(d,J=36.7Hz),137.21,137.19,136.53,136.43,134.67,133.95,133.64(d,J=4.8Hz),133.14,132.86(d,J=1.5Hz),132.43,132.31(d,J=2.0Hz),132.19,131.47,131.27(d,J=1.5Hz),129.10,128.83,128.74,128.41,128.35,128.31,127.85(d,J=2.3Hz),127.51,126.85,126.79,125.95,125.06,124.98,120.88,109.91,55.40,31.85(d,J=22.8Hz),30.85(d,J=17.0Hz),-3.29(d,J=11.0Hz);

[0564] 31 PNMR(243MHz,CDCl3)δ-3.43;

[0565] HRMS(ESI)m / zcalcdforC 36 H 32 OPSi[M+H] + 539.1955,found539.1954.

[0566] Example 25: Preparation of (4S,11bR)-4-(2-((S)-(2-Methoxyphenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5r) and (4R,11bS)-4-(2-((R)-(2-Methoxyphenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5q)

[0567]

[0568] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. o-MeO-C6H4SiHCl2 (345.4 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 hour. MeMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, which took 10 hours to 12 hours. Concentration was performed to obtain a crude reaction mixture. Using tetrachloroethane as an internal standard, the 1HNMR and 31P NMR analysis of the crude reaction mixture determined that the compound 5r in the crude reaction mixture had an 80% yield and 1.66:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. Concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5r·BH3 and compound 5q·BH3, respectively, and then compound 5r·BH3 and compound 5q·BH3 were mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product of compound 5r and a crude product of compound 5q. The crude products of compound 5r and compound 5q were concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5r (white foam, 235.9 mg, 44% yield, >99% de) and compound 5q (white foam, 151.4 mg, 28% yield), >99% de). The obtained compounds 5r and 5q were tested for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0569] Characterization of compound 5r:

[0570]

[0571] 1HNMR(400MHz, CDCl3)δ7.90(dd,J=8.4,3.4Hz,3H),7.74(d,J=8.3Hz,1H),7.65–7.53( m,2H),7.48(dt,J=7.2,1.4Hz,1H),7.46–7.33(m,3H),7.33–7.07(m,6H),6.97(t,J=7. 3Hz,1H),6.84(d,J=8.3Hz,1H),6.82–6.70(m,2H),5.34(m,1H),3.72(s,3H),2.98(d, J=11.4Hz,1H),2.82–2.57(m,2H),2.38(dd,J=14.2,3.8Hz,1H),0.70(d,J=3.8Hz,3H);

[0572] 13 CNMR(151MHz, CDCl3)δ164.40,143.28(d,J=8.6Hz),143.06(d,J=30.5Hz),137.30,136.19,136.09,134.6 6,134.01,133.75(d,J=4.6Hz),133.07,132.89,132.42,132.32,132.14,131.57,130.90,128.85,128.76, 128.58,128.41,128.37,128.32,127.89(d,J=2.2Hz),127.47,126.83,126.80,125.96,125.09,124.95,1 24.82 (d, J = 3.4Hz), 120.94, 110.01, 55.43, 31.86 (d, J = 22.4Hz), 30.38 (d, J = 17.4Hz), -3.44 (d, J = 9.3Hz);

[0573] 31 PNMR (162MHz,CDCl3)δ-3.16;

[0574] HRMS (ESI) m / zcalcdforC 36 H 32 OPSi[M+H] + 539.1955, found 539.1954.

[0575] Characterization of compound 5q:

[0576]

[0577] 1HNMR(600MHz,CDCl3)δ7.92(d,J=8.2Hz,1H),7.88(t,J=9.3Hz,2H),7.78(d,J=8.3Hz,1H),7.63(d,J=7.5Hz,1H),7.49(d,J=8.3Hz,1H),7.45–7.33(m,4H),7.31(t,J=7.4Hz,1H),7.28–7.10(m,5H),6.94(t,J=7.3Hz,1H),6.90(d,J=8.3Hz,1H),6.82(t,J=8.4Hz,2H),5.26(dq,J=7.4,3.8Hz,1H),3.71(s,3H),2.95(dd,J=11.9,2.0Hz,1H),2.68(ddd,J=17.7,12.1,4.7Hz,2H),2.37(dd,J=14.4,3.6Hz,1H),0.73(d,J=2.5Hz,2H);

[0578] 13 CNMR(151MHz,CDCl3)δ164.40,143.52(d,J=13.6Hz),143.29(d,J=36.7Hz),137.21,137.19,136.53,136.43,134.67,133.95,133.64(d,J=4.8Hz),133.14,132.86(d,J=1.5Hz),132.43,132.31(d,J=2.0Hz),132.19,131.47,131.27(d,J=1.5Hz),129.10,128.83,128.74,128.41,128.35,128.31,127.85(d,J=2.3Hz),127.51,126.85,126.79,125.95,125.06,124.98,120.88,109.91,55.40,31.85(d,J=22.8Hz),30.85(d,J=17.0Hz),-3.29(d,J=11.0Hz);

[0579] 31 PNMR(243MHz,CDCl3)δ-3.43;

[0580] HRMS(ESI)m / zcalcdforC 36 H 32 OPSi[M+H] + 539.1955,found539.1954.

[0581] Example 26: Preparation of Compound 5s and Compound 5s'

[0582]

[0583] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. 8-Lithioquinolyl (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that the crude reaction mixture had a total yield of 70% for compound 5s and compound 5s' and a dr of 1:1 (compound 5s:compound 5s'). The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The mixture was concentrated and purified by silica gel column chromatography (PE / DCM=100:1-3:1) to obtain 5s·BH3 (TLC upper spot) and 5s'·BH3 (TLC lower spot), respectively. Compounds 5s·BH3 and 5s'·BH3 were then mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude products were concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5s (white solid, 196.5 mg, 35% yield, >99% de) and compound 5s' (white solid, 158.4 mg, 28% yield, >99% de). The obtained compounds 5s and 5s' were tested for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0584] The characterization data corresponding to 5s are as follows:

[0585]

[0586] 1HNMR(400MHz,CDCl3)δ8.85(dd,J=4.2,1.8Hz,1H),8.07(dd,J=8.3,1.9Hz,1H),7.96(dd,J=6.7,1.5Hz,1H),7.86(dd,J=8.2,1.7Hz,3H),7.81(dd,J=8.2,1.5Hz,1H),7.68(d,J=8.4Hz,1H),7.58(td,J=8.1,3.4Hz,2H),7.51(dd,J=8.1,6.7Hz,1H),7.37(tdd,J=8.1,6.2,1.7Hz,2H),7.34–7.24(m,2H),7.26–7.11(m,4H),7.08(td,J=7.5,1.5Hz,1H),6.78(dd,J=7.7,2.8Hz,1H),6.75(d,J=8.3Hz,1H),5.79(dq,J=7.4,3.7Hz,1H),2.98(dd,J=11.7,1.7Hz,1H),2.78(dd,J=17.1,11.7Hz,1H),2.63(d,J=8.0Hz,2H),0.85(dd,J=3.8,0.9Hz,3H);

[0587] 13 CNMR(101MHz,CDCl3)δ152.46,149.55,143.48(d,J=43.3Hz),143.11(d,J=22.4Hz),138.41(d,J=3.4Hz),138.23,138.21,136.38(d,J=13.3Hz),136.21,134.67,134.19,134.17,133.78(d,J=4.5Hz),132.97,132.84(d,J=1.7Hz),132.37,132.27(d,J=2.1Hz),132.07,130.63,129.79,128.81,128.61,128.45,128.34,128.29,127.87(d,J=2.4Hz),127.77,127.41,126.77,126.31,125.92,125.89,125.04,124.87,121.03,31.78(d,J=22.6Hz),30.21(d,J=17.5Hz),-2.79(d,J=8.1Hz);

[0588] 31 PNMR(162MHz,CDCl3)δ-2.69;

[0589] HRMS (ESI) m / zcalcdforC 38 H 31 NPSi[M+H] + 560.1958, found 560.1956.

[0590] The characterization data corresponding to 5s' are as follows:

[0591]

[0592] 1 HNMR (400MHz, CDCl3) δ8.86 (dd, J=4.2, 1.8Hz, 1H), 8.09 (dd, J=8.3, 1.8Hz, 1H), 7.93 –7.78(m,5H),7.79–7.69(m,2H),7.47(dd,J=8.1,6.7Hz,1H),7.44–7.26(m,5H),7.2 6–7.10(m,5H),6.89–6.77(m,2H),5.71(dq,J=7.4,3.7Hz,1H),2.96(dd,J=11.8,1.9 Hz,1H),2.72–2.60(m,2H),2.37(dd,J=14.2,3.8Hz,1H),0.90(dd,J=3.8,1.2Hz,3H);

[0593] 13 CNMR (101MHz, CDCl3) δ152.54, 149.56, 143.65 (d, J = 10.0Hz), 143.31 (d, J = 12.8Hz), 138.54 (d, J = 3.8Hz), 138.21, 138.19 ,136.87(d,J=14.2Hz),136.23,134.61,133.93,133.63(d,J=4.7Hz),133.04,132.80(d,J=1.7Hz),132.40,132.25(d,J= 2.1Hz),132.13,131.18,131.16,129.66,129.07,128.79,128.72,128.34,128.30,127.79(d,J=2.4Hz),127.75,127.48, 126.80,126.76,126.32,125.91,125.03,124.94,120.96,31.96(d,J=22.8Hz),30.66(d,J=17.5Hz),-2.63(d,J=10.1Hz).

[0594] 31PNMR (162MHz,CDCl3)δ-3.53;

[0595] HRMS (ESI) m / zcalcdforC 38 H 31 NPSi[M+H] + 560.1958, found 560.1955.

[0596] Example 27: (4R,11bS)-4-(2-((S)-(2-(Diphenylphosphaneyl)phenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5t) and (4R,11bS)-4-(2-((S)-(2-

[0597] Preparation of (Diphenylphosphaneyl)phenyl)(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5t')

[0598]

[0599] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. o-Ph2P-C6H4Li (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31PNMR analysis determined that the compound 5t and compound 5t' in the crude reaction mixture had a 90% total yield and 2.1:1 dr (compound 5t: compound 5t'). The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (8.0 mL, 1.0 M in THF, 4.0 mmol, 8.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. Concentrated and purified by silica gel column chromatography (PE / DCM=100:1 to 1:1) to obtain compound 5t·BH3 and compound 5t'·BH3, respectively, and then compound 5t·BH3 and compound 5t'·BH3 were mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product of compound 5t and a crude product of compound 5t'. The crude products of compound 5t and compound 5t' were concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5t (white solid, 236.9 mg, 34% yield, >99% de) and compound 5t' (white solid, 126.1 mg, 18% yield, >99% de). The obtained compounds 5t and 5t' were tested for specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0600] Characterization of compound 5t:

[0601]

[0602]

[0603] 1 HNMR (400MHz, CDCl3) δ8.03–7.87(m,3H),7.77(d,J=7.2Hz,1H),7.69(d,J=8.3Hz, 1H),7.62(d,J=8.3Hz,1H),7.55(d,J=7.4Hz,1H),7.49–7.35(m,4H),7.32–7.17(m ,13H),7.17–7.06(m,4H),6.80–6.66(m,2H),5.86–5.69(m,1H),3.00(d,J=11.7Hz ,1H),2.74(dd,J=17.3,11.6Hz,1H),2.56(d,J=8.1Hz,2H),0.78(d,J=3.8Hz,3H);

[0604] 13CNMR (101 MHz, CDCl3) δ 144.89 (d, J = 3.8 Hz), 144.43 (d, J = 4.0 Hz), 143.96 (d, J = 4.0 Hz), 143.93 (d, J = 10.1 Hz), 143.52 (d, J = 3.3 Hz), 142.71 (d, J = 22.1 Hz), 137.84 (d, J = 11.7 Hz), 137.65 (d, J = 11.4 Hz), 136.83 (d, J = 1.0 Hz), 136.68 (d, J = 2.2 Hz), 136.58 (d, J = 1.8 Hz), 136.44 (d, J = 2.5 Hz), 134.67, 134.64, 134.12, 133.84 (d, J = 4.6 Hz), 133.71, 133.51, 133.32, 132.94, 132.88 (d, J = 1.8 Hz), 132.36, 132.29 (d, J = 2.1 Hz), 132.04, 130.63, 129.88, 129.09, 128.77, 128.65, 128.55, 128.54, 128.49, 128.37, 128.34, 128.31, 128.27, 127.92 (d, J = 2.3 Hz), 127.26, 126.83, 126.77, 125.94, 125.84, 125.08, 124.85, 31.01 (d, J = 22.0 Hz), 29.81 (d, J = 17.4 Hz), -2.95 (t, J = 7.6 Hz);

[0605] 31 PNMR (162 MHz, CDCl3) δ -2.91 (d, J = 3.6 Hz), -11.97 (d, J = 2.9 Hz);

[0606] HRMS (ESI) m / z calcd for C 47 H 39 P2Si [M + H] + 693.2291, found 693.2286.

[0607] Characterization of Compound 5t'

[0608]

[0609]

[0610] 1HNMR(400MHz,CDCl3)δ7.90(d,J=8.2Hz,2H),7.86(d,J=8.3Hz,1H),7.76(d,J=8.5Hz,2H),7.61–7.53(m,1H),7.40(m,2H),7.37–7.26(m,4H),7.26–7.19(m,6H),7.19–7.06(m,10H),6.80(dd,J=8.4,1.6Hz,1H),6.75(dd,J=7.6,2.4Hz,1H),5.62–5.51(m,1H),2.80(dt,J=11.8,2.1Hz,1H),2.57–2.40(m,2H),2.24(dt,J=14.3,2.7Hz,1H),0.76(t,J=3.0Hz,3H);

[0611] 13 CNMR(101MHz,CDCl3)δ145.53(d,J=4.5Hz),145.08(d,J=4.4Hz),143.84(d,J=3.7Hz),143.74,143.79(d,J=34.6Hz),143.37(d,J=3.8Hz),137.94(d,J=11.6Hz),137.37(d,J=11.6Hz),137.09(d,J=2.7Hz),136.94(d,J=2.8Hz),136.66(d,J=3.3Hz),136.52(d,J=3.2Hz),134.64,134.09,134.01,133.86,133.73,133.68,133.59(d,J=4.9Hz),133.54,133.03,132.79(d,J=1.7Hz),132.36,132.30(d,J=2.1Hz),132.14,131.28(d,J=2.1Hz),129.57,129.15,129.02,128.81,128.45,128.43,128.37,128.35,128.33,128.28,128.26,127.75(d,J=2.4Hz),127.46,126.80,125.95,125.90,125.06,124.94,31.51(d,J=23.4Hz),30.86(d,J=17.7Hz),-2.50(dd,J=10.3,7.0Hz);

[0612] 31 PNMR(162MHz,CDCl3)δ-3.54,-11.21;

[0613] HRMS (ESI) m / zcalcdforC 47 H 39 P2Si[M+H] + 693.2291, found 693.2285.

[0614] Example 28: Preparation of (4R,11bS)-4-(2-((S)-Methyl(2-(methylthio)phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5u)

[0615]

[0616] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. o-MeS-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5u in the crude reaction mixture had a 76% yield and a dr of 7:1. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5u·BH3, and then compound 5u·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by rapid silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5u (white foam, 300.7 mg, 54% yield, >99% de). The obtained compound 5u was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0617] Characterization of Compound 5u:

[0618]

[0619] 1 HNMR(600MHz,CDCl3)δ7.99–7.83(m,3H),7.77(d,J=8.3Hz,1H),7.73(d,J=7.4Hz,1H),7.52(d,J=7.4Hz,1H),7.45(d,J=8.3Hz,1H),7.41(m,2H),7.33(m,2H),7.29(d,J=7.8Hz,1H),7.26–7.21(m,2H),7.21–7.08(m,4H),6.89(d,J=8.3Hz,1H),6.80(d,J=7.8Hz,1H),5.35(m,1H),2.94(d,J=11.9Hz,1H),2.64(dd,J=17.1,11.8Hz,1H),2.55(t,J=13.2Hz,1H),2.33(s,3H),2.24(dd,J=14.6,3.7Hz,1H),0.80(d,J=3.8Hz,3H);

[0620] 13 CNMR(151MHz,CDCl3)δ145.18,143.58(d,J=22.5Hz),143.19(d,J=46.5Hz),138.02(d,J=4.4Hz),137.12,137.02,136.75,136.73,134.64,133.92,133.67(d,J=4.4Hz),133.06,132.85,132.43,132.32,132.16,131.27,130.43,129.13,129.07,128.90,128.39,128.34,128.32,127.83(d,J=2.4Hz),127.58,127.52,126.82,125.95,125.42,125.08,124.97,31.63(d,J=22.8Hz),30.72(d,J=17.3Hz),17.89,-2.99(d,J=11.3Hz);

[0621] 31 PNMR(243MHz,CDCl3)δ-2.72;

[0622] HRMS(ESI)m / zcalcdforC 36 H 32PSSi[M+H] + 555.1726, found 555.1725.

[0623] Example 29: Preparation of (4R,11bS)-4-(2-((S)-Dibenzo[b,d]thiophen-4-yl(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5v)

[0624]

[0625] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. Dibenzo[b,d]thienyl-4-ylmagnesium bromide (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5v in the crude reaction mixture had a 78% yield and 15:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5v·BH3, and then compound 5v·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5v (as a white solid, 373.8 mg, 61% yield, >99% de). The obtained compound 5v was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0626] Characterization of compound 5v:

[0627]

[0628] 1 HNMR(400MHz,CDCl3)δ8.14–7.98(m,2H),7.81(dd,J=9.5,8.0Hz,3H),7.73(dd,J=8.5,4.8Hz,2H),7.71–7.63(m,2H),7.43–7.26(m,7H),7.20(dd,J=8.7,1.3Hz,1H),7.17–7.10(m,2H),7.10–7.03(m,2H),6.78(dd,J=7.6,2.7Hz,1H),6.72(d,J=8.3Hz,1H),5.48(dq,J=7.5,3.8Hz,1H),2.90(dd,J=11.8,2.6Hz,1H),2.63–2.43(m,2H),2.04(dd,J=14.3,3.7Hz,1H),0.91(dd,J=3.9,1.6Hz,3H);

[0629] 13 CNMR(101MHz,CDCl3)δ146.23,144.19(d,J=21.8Hz),141.78(d,J=48.1Hz),139.72,137.22(d,J=15.2Hz),135.40,134.74,134.36,134.23(d,J=3.2Hz),133.59,133.57(d,J=5.6Hz),133.00,132.77(d,J=1.8Hz),132.36,132.21(d,J=2.1Hz),132.06,131.63(d,J=2.1Hz),131.30(d,J=4.7Hz),129.61,129.18,129.09,128.37,128.36,128.28,128.25,127.68,127.66,127.46,126.73,126.71,126.66,125.93,125.05,124.96,124.31,124.22,122.73,121.62,31.45(d,J=22.3Hz),30.72(d,J=16.8Hz),-3.51(d,J=12.8Hz);

[0630] 31 PNMR(162MHz,CDCl3)δ-2.77;

[0631] HRMS(ESI)m / zcalcdforC41 H 32 PSSi[M+H] + 615.1726, found 615.1722.

[0632] Example 30: Preparation of (4S,11bR)-4-(2-((R)-Butyl(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5w)

[0633]

[0634] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. n-BuMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5w in the crude reaction mixture had a 72% yield and 2:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere, and then stirred at room temperature for 12 hours, concentrated, and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5w·BH3, and then compound 5w·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5w (in the form of white foam, 177.4 mg, 36% yield, >99% de). The obtained compound 5w was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0635] Characterization of compound 5w:

[0636]

[0637] 1 HNMR(400MHz,CDCl3)δ7.92(dd,J=8.1,5.0Hz,3H),7.79(d,J=8.4Hz,1H),7.65(dd,J=8.4,1.1Hz,1H),7.61(dt,J=7.5,1.9Hz,1H),7.43(m,2H),7.34–7.19(m,5H),7.13(m,1H),6.91(d,J=8.4Hz,1H),6.80(dd,J=7.7,2.8Hz,1H),4.65(m,1H),3.04(dd,J=11.8,2.0Hz,1H),2.94–2.78(m,2H),2.60(dd,J=14.2,3.9Hz,1H),1.35(m,4H),1.08–0.91(m,2H),0.90–0.84(m,3H),0.45(dd,J=3.8,1.2Hz,3H);

[0638] 13 CNMR(151MHz,CDCl3)δ144.02(d,J=46.8Hz),143.31(d,J=21.9Hz),135.89(d,J=14.7Hz),134.57,133.76(d,J=4.8Hz),133.71,133.19,132.95(d,J=1.5Hz),132.51,132.38(d,J=2.3Hz),132.19,131.35(d,J=2.0Hz),129.07,128.84,128.78,128.56(d,J=1.5Hz),128.40,128.35,127.77(d,J=2.3Hz),127.58,126.86,126.82,126.06,126.02,125.16,125.05,32.37(d,J=22.3Hz),30.72(d,J=16.8Hz),27.16,26.34,14.79(d,J=9.3Hz),13.97,-3.79(d,J=9.7Hz);

[0639] 31 PNMR(162MHz,CDCl3)δ-4.08;

[0640] HRMS(ESI)m / zcalcdforC 33 H 34 PSi[M+H] +489.2162, found 489.2161.

[0641] Example 31: Preparation of (4R,11bS)-4-(2-((R)-Cyclohexyl(methyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5x)

[0642]

[0643] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. CyMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5x in the crude reaction mixture had a 66% yield and 3:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5x·BH3, and then compound 5x·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5x (in the form of white foam, 191.5 mg, 37% yield, >99% de). The obtained compound 5x was taken to detect the specific rotation, hydrogen spectrum, and carbon spectrum. 31 PNMR and mass spectrometry, etc., the results are as follows:

[0644] Characterization of compound 5x:

[0645]

[0646] 1 HNMR(600MHz,CDCl3)δ7.93(m,3H),7.78(d,J=8.2Hz,1H),7.65(d,J=8.3Hz,1H),7.59(d,J=7.4Hz,1H),7.47–7.38(m,2H),7.30(t,J=8.4Hz,2H),7.27–7.24(m,1H),7.23–7.19(m,2H),7.12(t,J=7.4Hz,1H),6.90(dd,J=8.4,1.8Hz,1H),6.81(d,J=7.7Hz,1H),4.49(d,J=4.5Hz,1H),3.03(d,J=11.7Hz,1H),2.94–2.74(m,2H),2.60(dt,J=14.4,3.2Hz,1H),1.69(m,5H),1.21(m,6H),0.43(d,J=6.0Hz,3H);

[0647] 13 CNMR(151MHz,CDCl3)δ143.41(d,J=12.3Hz),143.18(d,J=36.8Hz),136.36(d,J=14.6Hz),134.60,133.77(d,J=5.5Hz),133.76,133.16,132.94,132.50,132.37(d,J=2.1Hz),132.17,131.28,129.03,128.72,128.67,128.55,128.40,128.34,127.78(d,J=2.3Hz),127.57,126.85,126.82,126.06,126.01,125.16,125.03,32.38(d,J=22.6Hz),30.78(d,J=17.0Hz),29.16,28.17,28.10,28.04,27.00,25.21(d,J=8.0Hz),-5.77(d,J=10.4Hz);

[0648] 31 PNMR(243MHz,CDCl3)δ-3.48;

[0649] HRMS(ESI)m / zcalcdforC 35 H 36 PSi[M+H] + 515.2318,found515.2315.

[0650] Example 32: Preparation of (4R,11bS)-4-(2-((R)-Naphthalen-1-yl(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5y)

[0651]

[0652] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. 1-Naphthylmagnesium bromide (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5y in the crude reaction mixture had a 90% yield and 45:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5y·BH3, and then compound 5y·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by rapid silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5y (white solid, 451.9 mg, 73% yield, >99% de). The obtained compound 5y was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0653] Characterization of compound 5y:

[0654]

[0655] 1HNMR(400MHz,CDCl3)δ8.07(d,J=8.3Hz,1H),7.95–7.87(m,3H),7.84(d,J=8.2Hz,1H),7.78(t,J=8.1Hz,2H),7.66–7.59(m,2H),7.51(dt,J=6.9,1.3Hz,1H),7.47(m,1H),7.39(m,8H),7.27(d,J=8.4Hz,1H),7.24–7.07(m,6H),6.91–6.82(m,2H),6.36(dd,J=8.0,1.2Hz,1H),2.93(dd,J=11.8,2.3Hz,1H),2.55(ddd,J=36.7,15.7,11.9Hz,2H),2.16(dd,J=14.3,3.8Hz,1H);

[0656] 13 CNMR(101MHz,CDCl3)δ144.31(d,J=22.8Hz),141.08(d,J=46.4Hz),137.60(d,J=14.1Hz),137.41,136.96,136.52,134.59(d,J=4.4Hz),134.39,133.83,133.58(d,J=4.6Hz),133.39,133.12,133.01(d,J=5.8Hz),132.82(d,J=1.3Hz),132.43,132.23(d,J=2.0Hz),132.17,131.90,130.58,129.80,129.59,129.09,129.00,128.93,128.51,128.39,128.38,128.31,128.26,127.74(d,J=2.5Hz),127.54,126.83,126.72,126.27,125.98,125.93,125.83,125.40,125.06,125.01,31.20(d,J=22.6Hz),30.88(d,J=17.3Hz);

[0657] 31 PNMR(162MHz,CDCl3)δ-2.98;

[0658] HRMS(ESI)m / zcalcdforC 44 H 34 PSi[M+H] + 621.2162,found621.2158.

[0659] Example 33: Preparation of (4R,11bS)-4-(2-((R)-[1,1':3',1"-Terphenyl]-5'-yl(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5z)

[0660]

[0661] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. 3,5-di-Ph-C6H3MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5z in the crude reaction mixture had an 88% yield and a 10:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5z·BH3, and then compound 5z·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5z (white solid, 497.4 mg, 69% yield, >99% de). The obtained compound 5z was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0662] Characterization of compound 5z:

[0663]

[0664] 1 HNMR(400MHz,CDCl3)δ7.92(d,J=8.4Hz,1H),7.88–7.84(m,2H),7.84–7.76(m,4H),7.68(dt,J=7.3,2.5Hz,2H),7.62–7.57(m,4H),7.55(dt,J=7.8,1.8Hz,1H),7.46–7.28(m,13H),7.25–7.08(m,5H),7.00–6.88(m,2H),5.99(dd,J=8.7,3.4Hz,1H),2.92(dt,J=12.0,2.8Hz,1H),2.67–2.53(m,2H),2.30(dt,J=14.6,3.2Hz,1H);

[0665] 13 CNMR(101MHz,CDCl3)δ144.52(d,J=22.2Hz),141.34,141.10(d,J=48.5Hz),137.59,137.44,136.23,136.15(d,J=4.9Hz),134.63(d,J=5.2Hz),134.30,133.98,133.97,133.79,133.53(d,J=4.9Hz),133.24,132.85(d,J=1.0Hz),132.46,132.25(d,J=1.8Hz),132.21,132.09,129.81,129.21,129.06,128.93,128.48,128.34,128.30,128.27,127.73,127.64,127.57,127.53,127.47,126.86,126.74,126.02,125.97,125.08,125.07,31.33(d,J=12.3Hz),31.14(d,J=6.4Hz);

[0666] 31 PNMR(162MHz,CDCl3)δ-3.13;

[0667] HRMS(ESI)m / zcalcdforC 52 H 40 PSi[M+H] + 723.2631,found723.2626.

[0668] Example 34: Preparation of (4R,11bS)-4-(2-((R)-(4-Fluorophenyl)(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5aa)

[0669]

[0670] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. p-FC6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5aa in the crude reaction mixture had an 82% yield and a 15:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere, and then stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5aa·BH3, and then compound 5aa·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5aa (white solid, 401.5 mg, 68% yield, >99% de). The obtained compound 5aa was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 19 FNMR, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0671] Characterization of compound 5aa:

[0672]

[0673] 1 HNMR(400MHz,CDCl3)δ7.94–7.90(m,1H),7.87(t,J=7.9Hz,2H),7.79(d,J=8.3Hz,1H),7.57(m,4H),7.47–7.34(m,7H),7.30(m,1H),7.25–7.03(m,7H),6.89(d,J=8.4Hz,1H),6.85(m,1H),5.87(d,J=8.4Hz,1H),2.95(dd,J=11.8,2.7Hz,1H),2.69–2.52(m,2H),2.21(dd,J=14.4,3.7Hz,1H);

[0674] 13 CNMR(101MHz,CDCl3)δ164.16(d,J=248.9Hz),144.21(d,J=22.1Hz),140.98(d,J=47.2Hz),138.18(d,J=1.0Hz),138.10(d,J=2.0Hz),137.47(d,J=14.6Hz),136.12,136.10,134.65(d,J=4.8Hz),134.28,133.66,133.64(d,J=5.2Hz),133.16,132.87(d,J=2.0Hz),132.47,132.28(d,J=2.1Hz),132.19,132.01(d,J=2.0Hz),130.29(dd,J=5.5,3.8Hz),129.83,129.75,129.15,129.00,128.51(d,J=1.0Hz),128.35,128.32,128.23,127.71(d,J=2.2Hz),127.59,126.85,126.75,126.03,125.15,125.07,115.44,115.24,31.29(d,J=22.4Hz),30.91(d,J=16.8Hz);

[0675] 19 FNMR(377MHz,CDCl3)δ-111.03;

[0676] 31 PNMR(162MHz,CDCl3)δ-2.83;

[0677] HRMS(ESI)m / zcalcdforC 40 H 31 FPSi[M+H] +589.1911, found 589.1908.

[0678] Example 35: Preparation of (4R,11bS)-4-(2-((S)-(4-Fluorophenyl)(4-methoxyphenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ab)

[0679]

[0680] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. pF-C6H4SiHCl2 (390.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. p-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5ab had a 69% yield and 5:1 dr in the crude reaction mixture. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ab·BH3, and then compound 5ab·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ab (white solid, 224.1 mg, 36% yield, >99% de). The obtained compound 5ab was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 19 FNMR, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0681] Characterization of compound 5ab:

[0682]

[0683] 1 HNMR(600MHz,CDCl3)δ7.92(d,J=8.3Hz,1H),7.87(dd,J=11.3,8.3Hz,2H),7.79(d,J=8.3Hz,1H),7.59(t,J=7.1Hz,2H),7.48(t,J=8.5Hz,3H),7.45–7.37(m,3H),7.30(t,J=7.5Hz,1H),7.23(d,J=5.1Hz,2H),7.18(q,J=7.3Hz,2H),7.12(d,J=8.4Hz,1H),7.07(t,J=8.7Hz,2H),6.92(d,J=8.0Hz,2H),6.89(d,J=8.4Hz,1H),6.85(d,J=7.6Hz,1H),5.83(d,J=8.0Hz,1H),3.81(s,3H),2.94(d,J=11.9Hz,1H),2.68–2.53(m,2H),2.20(dd,J=14.3,3.5Hz,1H);

[0684] 13 CNMR(151MHz,CDCl3)δ164.12(d,J=249.0Hz),161.05,144.18(d,J=22.2Hz),141.41(d,J=47.2Hz),138.14,138.09,137.62,137.45(d,J=14.7Hz),134.33,133.69,133.64(d,J=5.3Hz),133.17,132.87,132.47,132.29(d,J=1.5Hz),132.20,131.99,130.82(t,J=4.1Hz),129.66,129.11,129.02,128.49,128.34,128.32,127.73(d,J=1.5Hz),127.59,126.85,126.76,126.02,125.14,125.06,115.43,115.29,113.99,55.21,31.35(d,J=22.6Hz),31.00(d,J=17.1Hz);

[0685] 19 FNMR(377MHz,CDCl3)δ-111.07;

[0686] 31PNMR (162MHz,CDCl3)δ-2.95;

[0687] HRMS (ESI) m / zcalcdforC 41 H 33 FOPSi[M+H] + 619.2017, found 619.2012.

[0688] Example 36: Preparation of (4R,11bS)-4-(2-((R)-(4-Methoxyphenyl)(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ac)

[0689]

[0690] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. p-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31PNMR analysis determined that compound 5ac in the crude reaction mixture had an 87% yield and a 12:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ac·BH3, and then compound 5ac·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ac (white solid, 419.4 mg, 70% yield, >99% de). The obtained compound 5ac was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0691] Characterization of compound 5ac:

[0692]

[0693] 1 HNMR (400MHz, CDCl3) δ7.91(d,J=8.2Hz,1H),7.86(t,J=8.5Hz,2H),7.78(d,J=8.4Hz,1H),7.63–7.57( m,2H),7.50(m,3H),7.45–7.33(m,6H),7.29(m,1H),7.24–7.21(m,2H),7.17(m,2H),7.12(d,J=8.4Hz, 1H),6.95–6.90(m,2H),6.88(d,J=8.3Hz,1H),6.86–6.82(m,1H),5.86(dd,J=8.1,1.9Hz,1H),3.81(s, 3H), 2.94 (dd, J=11.8, 2.4Hz, 1H), 2.60 (ddd, J=34.0, 15.4, 11.7Hz, 2H), 2.21 (dd, J=14.4, 3.6Hz, 1H);

[0694] 13CNMR(101MHz, CDCl3)δ160.97,144.18(d,J=22.4Hz),141.61(d,J=46.8Hz),137.71,137.70,137.50(d,J=14.5Hz),136 .13,135.29(d,J=4.6Hz),134.45,133.84,133.63(d,J=4.5Hz),133.12,132.84,132.44,132.28(d,J=2.0Hz),132.18, 131.86(d,J=1.0Hz),129.61,129.52,129.03,128.99,128.43,128.33,128.31,128.12,127.79(d,J=1.9Hz),127.54,1 26.84,126.75,125.97,125.31(d,J=5.5Hz),125.09,125.01,113.92,55.20,31.31(d,J=22.8Hz),30.95(d,J=17.3Hz);

[0695] 31 PNMR (162MHz,CDCl3)δ-2.69;

[0696] HRMS (ESI) m / zcalcdforC 41 H 34 OPSi[M+H] + 601.2111, found 601.2108.

[0697] Example 37: Preparation of (4R,11bS)-4-(2-((S)-(4-Methoxyphenyl)(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ad)

[0698]

[0699] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. p-MeO-C6H4SiHCl2 (414.3 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. PhMgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5ad in the crude reaction mixture had an 83% yield and 8:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ad·BH3, and then compound 5ad·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ad (as a white solid, 307.6 mg, 51% yield, >99% de). The obtained compound 5ad was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0700] Characterization of compound 5ad:

[0701]

[0702] 1HNMR(400MHz,CDCl3)δ7.94–7.83(m,3H),7.79(d,J=8.4Hz,1H),7.60–7.52(m,4H),7.49–7.33(m,7H),7.29(m,1H),7.26–7.21(m,2H),7.21–7.15(m,2H),7.12(d,J=8.4Hz,1H),6.97–6.91(m,2H),6.89(d,J=8.3Hz,1H),6.87–6.82(m,1H),5.86(d,J=8.1Hz,1H),3.80(s,3H),2.94(dd,J=11.8,2.4Hz,1H),2.60(ddd,J=31.1,15.6,11.9Hz,2H),2.22(dd,J=14.4,3.7Hz,1H);

[0703] 13 CNMR(151MHz,CDCl3)δ161.00,144.21(d,J=22.3Hz),141.60(d,J=46.8Hz),137.74,137.48(d,J=14.4Hz),136.09,135.28(d,J=5.4Hz),134.46,133.86,133.63(d,J=4.6Hz),133.14,132.86,132.44,132.28,132.19,131.88,129.54,129.52,129.05,128.99,128.44,128.34,128.31,128.07,127.79,127.55,126.85,126.76,125.98,125.97,125.37(d,J=4.6Hz),125.09,125.02,113.99,55.18,31.30(d,J=22.7Hz),30.97(d,J=17.1Hz);

[0704] 31 PNMR(162MHz,CDCl3)δ-2.85;

[0705] HRMS(ESI)m / zcalcdforC 41 H 34 OPSi[M+H] + 601.2111,found601.2107.

[0706] Example 38: Preparation of (4S,11bR)-4-(2-((R)-(2-Methoxyphenyl)(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ae)

[0707]

[0708] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. o-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5ae in the crude reaction mixture had an 80% yield and 11.5:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ae·BH3, and then compound 5ae·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ae (white solid, 320.2 mg, 53% yield, 88% de). The obtained compound 5ae was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0709] Characterization of compound 5ae:

[0710]

[0711] 1HNMR(600MHz,CDCl3)δ7.90(d,J=8.2Hz,1H),7.84(dd,J=14.0,8.3Hz,2H),7.77(d,J=8.4Hz,1H),7.62–7.57(m,2H),7.41(dddd,J=12.6,8.1,4.5,1.7Hz,4H),7.37–7.31(m,4H),7.28–7.19(m,4H),7.16–7.10(m,3H),6.93(t,J=7.3Hz,1H),6.87(dd,J=8.2,2.8Hz,2H),6.81(dd,J=7.7,2.5Hz,1H),5.92(d,J=8.2Hz,1H),3.65(s,3H),2.93(dd,J=11.8,2.1Hz,1H),2.64(dd,J=17.0,11.8Hz,1H),2.49(dd,J=14.4,12.1Hz,1H),2.15(dd,J=14.5,3.7Hz,1H);

[0712] 13 CNMR(151MHz,CDCl3)δ164.48,143.76(d,J=22.9Hz),141.57(d,J=45.9Hz),138.13,137.13(d,J=14.1Hz),136.25,135.40(d,J=4.3Hz),134.59,133.98,133.60(d,J=5.0Hz),133.08,132.81,132.39,132.25,132.16,131.86,131.54,129.36,129.15,129.07,128.71,128.35,128.31,128.29,127.94,127.85,127.47,126.82,126.73,125.93,125.90,125.02,124.94,123.17(d,J=5.5Hz),120.95,110.11,55.44,31.13(d,J=23.0Hz),30.93(d,J=17.4Hz);

[0713] 31 PNMR(243MHz,CDCl3)δ-2.46(minor),-2.81(major);

[0714] HRMS(ESI)m / zcalcdforC 41 H 34 OPSi[M+H] +601.2111, found 601.2107.

[0715] Example 39: Preparation of (4S,11bR)-4-(2-((R)-(2-Methoxynaphthalen-1-yl)(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5af)

[0716]

[0717] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. 2-Methoxy-1-naphthylmagnesium bromide (3.5 mmol, 3.5 equiv) was then added and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard to react the crude mixture. 1 HNMR and 31 PNMR analysis determined that compound 5af in the crude reaction mixture had a 94% yield and 40:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere, and then stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5af·BH3, and then compound 5af·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by rapid silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5af (white solid, 534.3 mg, 82% yield, 95% de). The obtained compound 5af was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 29 SiNMR, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0718] Characterization of compound 5af:

[0719]

[0720] 1 HNMR(600MHz,CDCl3)δ8.46–8.37(m,1H),8.00(d,J=8.9Hz,1H),7.95–7.88(m,2H),7.86(d,J=8.4Hz,1H),7.78(d,J=8.3Hz,1H),7.75–7.70(m,2H),7.57(d,J=8.4Hz,1H),7.52(dt,J=7.4,1.8Hz,1H),7.45–7.29(m,7H),7.25(dd,J=8.1,5.3Hz,2H),7.21–7.12(m,4H),7.12–7.07(m,2H),7.03(d,J=8.5Hz,1H),6.45(d,J=8.5Hz,1H),6.30(d,J=8.3Hz,1H),3.29(s,3H),2.79–2.67(m,2H),2.63(dd,J=11.6,3.0Hz,1H),1.84(dd,J=15.4,11.7Hz,1H);

[0721] 13 CNMR(151MHz,CDCl3)δ163.43,144.81(d,J=22.6Hz),143.44(d,J=47.3Hz),138.31,136.90(d,J=15.4Hz),136.34,135.34(d,J=7.5Hz),134.35,134.26,133.37,133.05,132.61,132.35,132.26,132.09,131.47,129.94,129.30,129.26,128.98,128.64,128.58,128.56,128.19,128.10,127.99,127.87,127.85,127.70,127.29,127.02,126.81,126.67,125.93,125.77,125.00,124.88,123.87,118.05(d,J=5.0Hz),113.88,56.06,32.22(d,J=17.1Hz),31.28(d,J=23.1Hz);

[0722] 29 SiNMR(80MHz,CDCl3)-34.1[d,J( 31 P- 29 Si)=25.1Hz]ppm

[0723] 31 PNMR(243MHz, CDCl3)δ-2.15(minor)-3.12(major);

[0724] HRMS (ESI) m / zcalcdforC 45 H 36 OPSi[M+H] + 651.2268, found 651.2267.

[0725] Example 40: Preparation of (4S,11bR)-4-(2-((R)-(2,6-Dimethoxyphenyl)(phenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ag)

[0726]

[0727] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. 2,6-di-MeO-C6H3MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31PNMR analysis determined that compound 5ag in the crude reaction mixture had a 92% yield and a 6:1 dr. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours, concentrated, and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ag·BH3, and then compound 5ag·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ag (white solid, 540.6 mg, 86% yield, 71% de). The obtained compound 5ag was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, the results are as follows:

[0728] Characterization of compound 5ag:

[0729]

[0730] 1 HNMR(600MHz, CDCl3)δ7.98–7.76(m,4H),7.73–7.60(m,2H),7.53–7.29(m, 7H),7.28–7.17(m,4H),7.17–7.04(m,4H),6.95(d,J=7.6Hz,1H),6.52(dd, J=60.3,8.2Hz,2H),6.05–5.93(m,1H),3.54(s,6H),2.99–2.78(m,1H),2.7 8–2.63(m,1H),2.53(dd,J=14.6,3.1Hz,1H),2.34(dd,J=16.0,11.7Hz,1H);

[0731] 13CNMR(151MHz, CDCl3)δ165.55,144.15(d,J=22.1Hz),143.54(d,J=46.5Hz),136.75,136.65,136.34,136.32 (d,J=6.3Hz),136.23(d,J=6.7Hz),134.77,134.42,133.43(d,J=5.1Hz),133.23,132.73,132.66,132.38,13 2.26,131.38,129.32,129.00,128.66,128.42,128.25,128.18,127.80,127.67,127.62,127.60,126.83,126 .78,125.91,125.86,124.94,111.57(d,J=5.4Hz),104.38,55.66,32.09(d,J=17.2Hz),31.29(d,J=23.9Hz);

[0732] 31 PNMR(243MHz, CDCl3)δ-2.16(minor),-3.23(major);

[0733] HRMS (ESI) m / zcalcdforC 42 H 36 O2PSi[M+H] + 631.2217, found 631.2212.

[0734] Example 41: Preparation of (4R,11bS)-4-(2-((R)-(2-(dimethylsilyl)phenyl)(4-methoxyphenyl)silyl)phenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ah)

[0735]

[0736] Referring to Experimental Procedure D, compound 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 mL). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. p-MeOC6H4SiHCl2 (414.3 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another hour. o-Me2SiH-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5ah in the crude reaction mixture had a 76% yield and 33:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ah·BH3, and then compound 5ah·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ah (white solid, 440.1 mg, 67% yield, >99% de). The obtained compound 5ah was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, the results are as follows:

[0737] Characterization of compound 5ah:

[0738]

[0739] 1HNMR(400MHz,CDCl3)δ7.90(d,J=8.2Hz,1H),7.86(d,J=8.2Hz,1H),7.83(d,J=8.3Hz,1H),7.77(d,J=8.3Hz,1H),7.65(dd,J=7.4,1.3Hz,1H),7.51–7.45(m,2H),7.42–7.30(m,6H),7.23(m,4H),7.18–7.09(m,3H),6.90(m,4H),6.16(d,J=7.6Hz,1H),4.60(p,J=3.7Hz,1H),3.77(s,3H),2.89(dd,J=11.8,2.2Hz,1H),2.63–2.49(m,2H),2.32(dd,J=14.4,3.7Hz,1H),0.24(d,J=3.7Hz,3H),0.17(d,J=3.7Hz,3H).

[0740] 13 CNMR(101MHz,CDCl3)δ160.88,145.44,144.17(d,J=23.1Hz),142.24(d,J=37.2Hz),141.99(d,J=3.3Hz),137.87,137.60(d,J=13.9Hz),137.08,137.06,134.60,134.56,134.01,133.54(d,J=4.7Hz),133.11,132.80(d,J=1.5Hz),132.39,132.24(d,J=2.1Hz),132.16,131.67(d,J=1.8Hz),129.33,128.97,128.72,128.70,128.32,128.28,127.82,127.79,127.55,126.82,126.76,125.94,125.91,125.82(d,J=4.8Hz),125.03,124.97,113.95,55.10,31.24(d,J=20.7Hz),31.03(d,J=15.0Hz),-2.61,-2.78.

[0741] 31 PNMR(162MHz,CDCl3)δ-2.80.

[0742] HRMS(ESI)m / zcalcdforC 43 H 40 OPSi2[M+H] + 659.2350,found659.2349.

[0743] Example 42: Preparation of (4S,11bR)-4-(2-((R)-Naphthalen-1-yl(phenyl)silyl)phenyl)-2,6-diphenyl-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepine (Compound 5ai)

[0744]

[0745] Referring to Experimental Procedure D, THF (5.0 mL) was added to a Schlenk flask containing 1b (619.5 mg, 1.0 mmol, 1.0 equiv) at room temperature. The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and then stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and the solution was cooled to -116 °C. PhSiHCl2 (354.2 mg, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 h. 1-Naphthylmagnesium bromide (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature. Concentrate to obtain a crude reaction mixture. Tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5ai in the crude reaction mixture had a 65% yield and 49:1 dr. The crude reaction mixture was then cooled to 0°C, and then BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere and stirred at room temperature for 12 hours. The reaction was concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5ai·BH3, and then compound 5ai·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5ai (white solid, 333.9 mg, 43% yield, 96% de). The obtained compound 5ai was taken to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0746] Characterization of compound 5ai:

[0747]

[0748] 1 HNMR(600MHz,CDCl3)δ7.95–7.88(m,3H),7.85(dd,J=8.2,3.8Hz,2H),7.79(s,1H),7.71(s,1H),7.49(d,J=7.6Hz,2H),7.47–7.02(m,26H),6.65(dd,J=6.3,2.6Hz,1H),6.04(d,J=9.2Hz,1H),3.05(dd,J=14.5,4.2Hz,1H),2.90(d,J=11.9Hz,1H),2.71(dd,J=16.0,11.8Hz,1H),2.55(dd,J=14.6,11.3Hz,1H);

[0749] 13 CNMR(151MHz,CDCl3)δ143.00(d,J=21.9Hz),141.36,141.34,140.95,140.67(d,J=45.9Hz),140.32(d,J=1.9Hz),137.85,137.75,137.44,136.80,136.20,134.74(d,J=4.5Hz),134.37(d,J=5.3Hz),134.18,133.30,132.62(d,J=4.5Hz),132.52,132.28,132.08,131.85,131.73(d,J=1.3Hz),131.56,130.81,130.26,130.03,129.99,129.75,129.61,129.37,129.33,128.83,128.80,128.70,128.58,128.35,128.26,128.01,128.00,127.89,127.07,126.76,126.68,126.45,126.07,125.97,125.64,125.53,125.38,27.16(d,J=25.4Hz),26.63(d,J=18.2Hz);

[0750] 31 PNMR(243MHz,CDCl3)δ-1.83;

[0751] HRMS(ESI)m / zcalcdforC 56 H 42 PSi[M+H] + 773.2788,found773.2782.

[0752] Example 43: Preparation of (2-((2-(Dimethylsilyl)phenyl)(methyl)silyl)phenyl)diphenylphosphane (racemicPSiSi)

[0753]

[0754] Referring to Experimental Procedure D, compound 1c (341.2 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (10.0 mL). The reaction mixture was cooled to -78 ° C, n-BuLi (0.44 mL, 2.5 M hexane solution, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere, and stirred at -78 ° C for 1 hour. MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was then added and the solution was stirred at -78 ° C for another hour. o-Me2SiH-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 hours to 12 hours to warm to room temperature. The reaction was concentrated and purified by silica gel column chromatography (PE / EA (V:V) = 100: 1 to 30: 1); dried to obtain the compound racemicPSiSi (as a white solid, 278.5 mg, 63% yield). The obtained compound racemicPSiSi was used to detect the specific rotation, hydrogen spectrum, carbon spectrum, 31 PNMR and mass spectrometry, etc., the results are as follows:

[0755] Characterization of racemicPSiSi compounds:

[0756] 1 HNMR (600MHz, CDCl3) δ7.64–7.44(m,3H),7.35–7.07(m,15H),5.53(s,1H),4.50(s,1H),0.66(s,3H),0.20(s,3H),0.13(s,3H).

[0757] 13CNMR (151MHz, CDCl3) δ144.92, 144.38 (d, J = 46.0Hz), 144.09 (d, J = 10.7Hz), 143.10 (d, J = 4.4Hz), 137.79 (d, J = 11.6Hz), 137.53 (d, J = 11.5Hz), 136. 55(d,J=14.9Hz),136.02,134.48,134.34,133.74,133.64,133.62,133.5 2,129.82,128.52,128.48,128.46,128.41,128.34,-2.69,-2.74,-2.80.

[0758] 31 PNMR (243MHz,CDCl3)δ-11.47.

[0759] HRMS (ESI) m / zcalcdforC 27 H 29 PSi2[M+H] + 441.1618, found 441.1617.

[0760] Example 44: Reaction Condition Screening Investigation Data

[0761]

[0762] Preparation methods of Experiments 1 to 3:

[0763] 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with solvent (10.0 ml). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere; and then stirred at -84 °C for 1 hour. MeSiHCl2 (see 2a in Table 1 for the amount of feed) was added and the solution was stirred at -84 °C for another hour. Then p-MeO-C6H4MgBr (see Table 1 for the amount of feed) was added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature; it was concentrated to obtain a crude reaction mixture; tetrachloroethane was used as an internal standard, and the crude reaction mixture was 1 HNMR and 31 The yield and diastereoselectivity (dr) of compound 5a in the crude reaction mixture were determined by PNMR analysis. The results are shown in Table 1.

[0764] Preparation method of experiment 4:

[0765] 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (with THF and Et2O as solvent, the total volume of the solvent was 10.0 mL, and the volume ratio of THF to Et2O was shown in Table 1). The reaction mixture was cooled to -84°C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere; and then stirred at -84°C for 1 hour. Then Et2O (with THF and Et2O as solvent, the total volume of the solvent was 10.0 mL, and the volume ratio of THF to Et2O was shown in Table 1) was added dropwise, and then MeSiHCl2 (the amount of the feed is shown in 2a in Table 1) was added and the solution was stirred at -84°C for another 1 hour. Then, p-MeO-C6H4MgBr (feeding amount see Table 1) was added, and the solution was gradually heated to room temperature, and the temperature was raised to room temperature for 10 hours to 12 hours; concentrated to obtain a crude reaction mixture; tetrachloroethane was used as an internal standard, and the crude reaction mixture was 1 HNMR and 31 The yield and diastereoselectivity (dr) of compound 5a in the crude reaction mixture were determined by PNMR analysis. The results are shown in Table 1.

[0766] Preparation methods of Experiments 5 to 7:

[0767] 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (with THF and Et2O as solvents, the total volume of the solvent was 10.0 mL, and the volume ratio of THF to Et2O was shown in Table 1). The reaction mixture was cooled to -84°C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere; and then stirred at -84°C for 1 hour. Then Et2O (with THF and Et2O as solvents, the total volume of the solvent was 10.0 mL, and the volume ratio of THF to Et2O was shown in Table 1) was added dropwise and cooled to -116°C; MeSiHCl2 (the amount of the feed is shown in 2a in Table 1) was added and the solution was stirred at -116°C for another 1 hour. Then, p-MeO-C6H4MgBr (feeding amount see Table 1) was added, and the solution was gradually heated to room temperature, and the temperature was raised to room temperature for 10 hours to 12 hours; concentrated to obtain a crude reaction mixture; tetrachloroethane was used as an internal standard, and the crude reaction mixture was 1 HNMR and 31 The yield and diastereoselectivity (dr) of compound 5a in the crude reaction mixture were determined by PNMR analysis. The results are shown in Table 1.

[0768] Preparation method of experiment 8:

[0769] 1a (467.3 mg, 1.0 mmol, 1.0 equiv) was mixed with THF (5.0 ml). The reaction mixture was cooled to -84 °C, and n-BuLi (0.44 mL, 2.5 M in n-hexane, 1.1 mmol, 1.1 equiv) was added dropwise under an argon atmosphere; and stirred at -84 °C for 1 hour. Et2O (5.0 mL) was then added dropwise and cooled to -116 °C; MeSiHCl2 (210 μl, 2.0 mmol, 2.0 equiv) was added and the solution was stirred at -116 °C for another 1 hour. p-MeO-C6H4MgBr (3.5 mmol, 3.5 equiv) was then added, and the solution was gradually warmed to room temperature, and it took 10 to 12 hours to warm to room temperature; it was concentrated to obtain a crude reaction mixture; tetrachloroethane was used as an internal standard, and the crude reaction mixture was purified by 1 HNMR and 31 PNMR analysis determined that compound 5a had an 83% yield and 11:1 dr in the crude reaction mixture. The crude reaction mixture was then cooled to 0°C, and then a BH3 solution (4.0 mL, 1.0 M in THF, 4.0 mmol, 4.0 equiv) was added under an argon atmosphere; then stirred at room temperature for 12 hours, concentrated and purified by silica gel column chromatography (PE / DCM (V:V) = 100:1 to 3:1) to obtain compound 5a·BH3, and then compound 5a·BH3 was mixed with a toluene (5.0 mL) solution of DABCO (6.0 equiv) at 50°C for 6 hours to obtain a crude product. The crude product was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1); dried to obtain compound 5a (313.5 mg, in the form of white foam, 58% yield, >99% de), the results are shown in Table 1.

[0770] Table 1: Results of Experiments 1 to 8

[0771]

[0772] In the table, 5a / 3a' represents the molar ratio of compound 5a and compound 3a' in the product; 5adr represents the yield ratio of compound 5a to compound 5a' in the product; the ratio in the solvent represents the volume ratio, such as THF / Et2O (1:1) means that the volume ratio of THF to Et2O is 1:1, and the same applies to other solvents.

[0773] Compound 3a':

[0774] Conclusion: From the above results, we can know that:

[0775] (1) Compared with other solvents, using THF as a solvent or a mixed solvent of THF and Et2O as a solvent is beneficial to improving the yield of the product and the diastereoselectivity of the product, among which the mixed solvent of THF and Et2O is more beneficial to improving the yield of the product and the diastereoselectivity of the product.

[0776] (2) The volume ratio of THF to Et2O in the mixed solvent of THF and Et2O is preferably 1:1, which is more conducive to improving the yield and diastereoselectivity of the product.

[0777] (3) Compared with other reaction temperatures, -116°C is more conducive to improving the yield and diastereoselectivity of the product.

[0778] (4) Adding BH3 to the crude product for reaction and then removing BH3 with DABCO is more conducive to improving the yield of the product and the enantiomeric purity of each diastereoisomer product.

[0779] Example 45: Performance of Chiral Silyl Ligands in Intermolecular Enantioselective C—H Silylation

[0780]

[0781] Referring to the above general procedure E, in a glove box filled with argon, [Ir(OMe)(cod)]2 (1.6 mg, 0.0025 mmol), 0.005 mmol chiral ligand (Compound L1, Compound L2, Compound L3, Compound L4 (Compound L1 to Compound L4 are commercially available ligands), Compound 5ah) or racemic ligand compound racemicPSiSi, and anhydrous toluene (0.4 mL) were placed in a dried 5 mL microwave reaction tube. After stirring at room temperature for 5-10 minutes, Compound 6 (0.10 mmol, 25.5 mg), Compound 7 (dimethyl(phenyl)silane) (0.20 mmol, 27.3 mg), 3,3-dimethyl-1-butene (0.20 mmol, 16.8 mg) and toluene (0.4 mL) were added. The tube was capped and taken out of the glove box. The resulting mixture was stirred at 60°C for 12 hours; then concentrated and purified by rapid silica gel column chromatography (PE / EA (V:V) = 60:1) to obtain compound (-)-8 (white solid). The enantiomeric excess (ee value) was determined by HPLC analysis using a Chiralpak IA column. The product yield and enantiomeric excess (ee value) results are shown in Table 2. (HPLC conditions: IA, wavelength = 254 nm, eluent: n-hexane / isopropanol = 95:5, flow rate = 1.0 mL / min, column temperature = 28°C, retention time (main peak) = 5.7 minutes, retention time (minor peak) = 6.7 minutes).

[0782] The obtained compound (-)-8 was tested for specific rotation, hydrogen spectrum, carbon spectrum and mass spectrum, and the results were as follows:

[0783] Characterization of Compound (-)-8:

[0784]

[0785] 1 HNMR(600MHz, CDCl3) δ8.61(dd,J=5.9,2.3Hz,1H),7.91(dd,J=8.4,2.2Hz,1H),7.87(dd,J =8.4,2.2Hz,1H),7.79(dd,J=8.3,2.2Hz,1H),7.73(dd,J=8.5,2.2Hz,1H),7.65(dd,J=6.1 ,2.2Hz,1H),7.58–7.53(m,1H),7.45–7.40(m,1H),7.24(s,1H),7.22–7.16(m,4H),7.15–7 .09(m,1H),7.06(dt,J=8.6,4.3Hz,2H),6.96(d,J=8.6Hz,1H),0.16(s,3H),-0.03(s,3H).

[0786] 13 CNMR(151MHz, CDCl3)δ161.45,144.02,142.15,138.27,135.91,135.73,133.83,133.77,132.58,131.54,130.11, 129.32,128.57,127.98,127.95,127.51,127.41,127.09,126.73,126.43,126.40,126.24,120.72,-1.09,-1.77.

[0787] HRMS (EI, m / z) calculation for C 27 H 24 NSi[M + ]:390.1673,found:390.1671.

[0788] result:

[0789] Table 2: Product yield and ee value results of different chiral ligands

[0790]

[0791]

[0792] Example 46: Preparation of Compound 7

[0793] Compound (-)-8 can be used to prepare compound 7, which is a commonly used N, O ligand (QUINOL) and is a commercial product.

[0794]

[0795] To a solution of compound (-)-8 (38.9 mg, 0.1 mmol) in THF (1.0 mL) was added TBAF (tetrabutylammonium fluoride) (1.0 M THF solution, 1.0 mL) at 0°C. The addition took 15 minutes to complete. Methanol (0.5 mL), KHCO3 (50.0 mg) and a 30% vol aqueous solution of H2O2 (0.6 mL) were then added to obtain a reaction mixture. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with 15 mL of ethyl acetate and quenched with a 3 mol / L aqueous solution of NaHSO4 (2.0 mL) at 0°C. The layers were separated, the organic layer was taken, the organic layer was washed with brine, and then dried with MgSO4, filtered, and the solvent was evaporated to obtain a residue. The residue was purified by flash silica gel column chromatography (petroleum ether:ethyl acetate (V / V)=5:1) to obtain compound 7 (white solid, 24.1 mg, 89% yield). The enantiomeric excess of compound 7 was determined to be 92% ee by HPLC analysis using a Chiralpak IA column. (HPLC conditions: wavelength = 250 nm, eluent: n-hexane / isopropanol (V / V) = 95:5, flow rate = 1.0 mL / min, column temperature = 28°C, retention time (main peak) = 28.9 min, retention time (secondary peak) = 22.8 min). The obtained compound 7 was tested for hydrogen spectrum, carbon spectrum and mass spectrum, and the results were as follows:

[0796] 1 H NMR (400MHz, DMSO) δ9.70(s,1H),8.60(d,J=6.0Hz,1H),8.05(d,J=8.4Hz,1H),7.95(d,J=8.4Hz,1H),7.91–7.88( m,2H),7.74(t,J=8.0Hz,1H),7.49–7.42(m,2H),7.36(d,J=8.8Hz,1H),7.29–7.19(m,2H),6.84(d,J=8.4Hz,1H);

[0797] 13C NMR(101MHz,DMSO)δ157.9,152.7,142.5,135.8,133.8,130.3,129.8,128.0,128 .0,127.8,127.4,127.0,126.9,126.4,123.9,122.7,120.0,118.4,118.3,39.5;

[0798] HRMS(EI,m / z)calcd for C 19 H 14 NO[M+H] + :272.1070,found:272.1068.

[0799] Example 47: Synthesis of Chiral Silicon-Based Ions and Preliminary Chiral Memory Studies

[0800]

[0801] In a glove box under an argon atmosphere, a dry J. Young NMR tube was loaded with triphenyl tetrakis(pentafluorophenyl)borate (CAS No.: 136040-19-2) (36.8 mg, 0.04 mmol, 1.0 equiv), compound ( Si R)-5af (26.0 mg, 0.04 mmol, 1.0 equiv) and 1,2-Cl2C6D4 (0.2 mL). After stirring at room temperature for 12 hours, the product was obtained. 1 H NMR, 29 Si NMR and 31 P NMR spectral analysis, the compound ( Si R)-9 (95% NMR yield and 90:10 dr, the yield was determined using triphenylmethane as an internal standard, dr was determined by 31 P NMR analysis). Then, LiAlH4 solution (0.016 mL, 2.5 M in THF, 0.04 mmol, 1.0 equiv) was added to the solution at -78°C, and the solution was gradually warmed to room temperature and stirred for 12 hours to obtain a crude reaction mixture. 31 P NMR analysis confirmed the presence of the returned compound ( Si R)-5af (86:14dr), and then the crude reaction mixture was concentrated and purified by flash silica gel column chromatography (PE / EA (V:V) = 100:1) to give compound ( Si R)-5af (white solid, 17.7 mg, 68% yield, 86:14 dr).

[0802] Take the obtained compound ( Si R)-5af and compound ( Si R)-5af detection hydrogen spectrum, 11 BNMR, 19 FNMR, 29 SiNMR and 31 PNMR et al., the results are as follows:

[0803] ( Si R)-9 Characterization:

[0804] 1 HNMR(400MHz,1,2-Cl2C6D4)δ8.01–7.82(m,4H),7.75(m,1H),7.57(m,4H),7.48–7.25(m,7H),7.24–7.00(m,26H),6.96(d,J=2.7Hz,1H),6.89 (s,1H),6.66–6.55(m,1H),4.10–4.03(m,0.33H),3.55(s,3H),3.36(q,J=7.1Hz,0.53H),3.29–3.07(m,2.54H),2.80(dd,J=14.9,4.3Hz,1H).

[0805] 11 BNMR(128MHz,1,2-Cl2C6D4)δ-16.24.

[0806] 19 FNMR(377MHz,1,2-Cl2C6D4)δ-131.59(8F,m),-162.17(4F,m),-166.01(8F,m).

[0807] 29 SiNMR(80MHz,1,2-Cl2C6D4)δ8.48[d,J( 31 P- 29 Si)=48.7Hz].

[0808] 31 PNMR(162MHz,1,2-Cl2C6D4)δ35.66(minor),29.13(major).

[0809] ( Si R) Characterization of -5af:

[0810] 1HNMR(600MHz,DMSO-d6)δ8.28(d,J=7.4Hz,0.81H),8.17(d,J=9.2Hz,1H),8.03( dd,J=7.3,2.4Hz,0.85H),8.01–7.86(m,3.17H),7.82–7.75(m,0.38H),7.69–7. 63(m,2.33H),7.62–7.59(m,0.35H),7.52(d,J=8.3Hz,0.22H),7.47–7.34(m,8. 65H),7.34–7.28(m,2H),7.26–7.11(m,3.32H),7.03(dt,J=7.4,1.9Hz,0.82H),7 .00(d,J=8.6Hz,0.17H),6.96–6.91(m,0.81H),6.86(dd,J=8.5,3.3Hz,1H),6.5 4(d,J=8.4Hz,0.16H),6.36(d,J=8.3Hz,0.78H),6.34(d,J=7.7Hz,0.77H),6.30( d,J=6.8Hz,0.15H),3.59(s,0.42H),3.32(s,2.54H),2.86–2.76(m,1H),2.48–2 .45(m,1H),1.94(dd,J=15.2,11.5Hz,0.87H),1.72(dd,J=14.2,11.9Hz,0.15H).

[0811] 31 PNMR(243MHz,DMSO-d6)δ-2.56(minor),-3.32(major).

[0812] 29 SiNMR(80MHz,DMSO-d6)δ-34.3[d,J( 31 P- 29 Si)=24.2Hz]ppm.

[0813] Conclusion: It can be seen from the above Example 47 that the compounds provided by the present invention are a class of potential silicon cation precursor reagents and are expected to be used in chiral silicon cation chemistry; chiral silicon cations are a class of strong chiral Lewis acid catalysts, and the compounds provided by the present invention can also be used in the field of asymmetric catalysis.

[0814] The method of the present invention has been described through preferred embodiments, and relevant personnel can obviously modify or appropriately change and combine the methods and applications described herein within the content, spirit and scope of the present invention to implement and apply the technology of the present invention. Those skilled in the art can refer to the content of this article and appropriately improve the process parameters. It is particularly important to point out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention.

Claims

1. A compound of formula I, in, R1 and R3 are each independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; R2 and R4 are each independently selected from H or substituted or unsubstituted aryl; Optionally, the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2.

2. The compound according to claim 1, wherein the structure of the compound represented by formula I is selected from the compound represented by formula I-0 or the compound represented by formula II-0: and / or The compound represented by formula II-0 is selected from the compound represented by formula II-1, and / or The compound represented by formula II-1 is selected from the compound represented by formula III-1 or the compound represented by formula III-2: Wherein Ar is a substituted or unsubstituted C6-C 20 Aryl.

3. A compound according to any one of claims 1 to 2, In the compound of formula I, the compound of formula I-0, the compound of formula II-0 or the compound of formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 alkyl; or In the compound represented by formula I, the compound represented by formula I-0, the compound represented by formula II-0 or the compound represented by formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 heteroaryl; or In the compound represented by formula I, the compound represented by formula I-0, the compound represented by formula II-0 or the compound represented by formula II-1, R2 and R4 are substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 Heteroaryl; R1, R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 alkyl; or In the compound represented by formula I, the compound represented by formula I-0, the compound represented by formula II-0 or the compound represented by formula II-1, R2 and R4 are substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 Heteroaryl; R1, R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl; or In the compound represented by formula III-1, R1 and R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 Alkyl; or In the compound represented by formula III-1, R1 and R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 heteroaryl; or In the compound represented by formula III-2, Ar is a substituted or unsubstituted C6-C 20 Aryl; R1, R3 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl or C1-C 10 Alkyl; or In the compound represented by formula III-2, Ar is a substituted or unsubstituted C6-C 20 Aryl; R1, R3 are each independently selected from substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 20 heteroaryl; or C1-C 20 The alkyl group is C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, C 10 Alkyl, C 11 Alkyl, C 12 Alkyl, C 13 Alkyl, C 14 Alkyl, C 15 Alkyl, C 16 Alkyl, C 17 Alkyl, C 18 Alkyl, C 19 Alkyl or C 20 Alkyl; or The C1-C 10 The alkyl group is C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl or C 10 Alkyl; or The C6-C 20 The aryl group is C6 aryl, C7 aryl, C8 aryl, C9 aryl, C 10 Aryl, C 11 Aryl, C 12 Aryl, C 13 Aryl, C 14 Aryl, C 15 Aryl, C 16 Aryl, C 17 Aryl, C 18 Aryl, C 19 Aryl or C 20 Aryl; or The C6-C 20 The heteroaryl group is C6 heteroaryl, C7 heteroaryl, C8 heteroaryl, C9 heteroaryl, C 10 Heteroaryl, C 11 Heteroaryl, C 12 Heteroaryl, C 13 Heteroaryl, C 14 Heteroaryl, C 15 Heteroaryl, C 16 Heteroaryl, C 17 Heteroaryl, C 18 Heteroaryl, C 19 Heteroaryl or C 20 heteroaryl; or The heteroaryl group has at least one heteroatom in the ring; or The heteroatoms include oxygen, sulfur or nitrogen.

4. The compound according to any one of claims 1 to 3, wherein R1, R2, R3, R4 or Ar is selected from the following groups: (1) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, - CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, - C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, - CH2CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3 , -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, - C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; or (2) In the compound represented by formula III-1, R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, - CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, - CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, - CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; or (3) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (4) In the compound represented by formula III-1, R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are each independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphine, thiomethyl or -SiH(CH3)2; or (5) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (6) In the compound represented by formula III-1, R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (7) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (8) In the compound represented by formula III-1, R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (9) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl; or (10) In the compound represented by formula III-1, R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl; or (11) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (12) In the compound represented by formula III-1, R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (13) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (14) In the compound represented by formula III-1, R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (15) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are H; R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (16) In the compound represented by formula III-1, R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (17) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, - CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, - C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, - CH2CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3 , -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, - C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl; or (18) In the compound represented by formula III-2, Ar is phenyl; R1 and R3 are each independently selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, - CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, - C(CH3)2CH2CH3, -CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, - CH2CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3 , -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, - C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl; or (19) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are each independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (20) In the compound represented by formula III-2, Ar is phenyl; R1 and R3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are each independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (twenty one) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (twenty two) In the compound represented by formula III-2, Ar is phenyl; R1 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (twenty three) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (twenty four) In the compound represented by formula III-2, Ar is phenyl; R3 is selected from methyl, ethyl, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -CH2CH(CH3)2, -CH(CH3)CH2CH3, -C(CH3)3, -CH2CH2CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH3)CH2CH2CH3, -CH(CH2CH3)2, -C(CH3)2CH2CH3, - CH(CH3)CH(CH3)2, -CH2CH2CH(CH3)2, -CH2CH(CH3)CH2CH3, -CH2CH2CH2CH2CH2CH3, - CH(CH3)CH2CH2CH2CH3, -CH(CH2CH3)(CH2CH2CH3), -C(CH3)2CH2CH2CH3, -CH(CH3)CH(CH3)CH2CH3, -CH(CH3)CH2CH(CH3)2, -C(CH3)(CH2CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH2CH3)CH(CH3)2, -C(CH3)2CH(CH3)2, -CH(CH3)C(CH3)3, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl; and / or the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (25) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, and cyclohexyl; or (26) In the compound represented by formula III-2, Ar is phenyl; R1 and R3 are each independently selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; or (27) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (28) In the compound represented by formula III-2, Ar is phenyl; R1 and R3 are each independently selected from cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (29) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (30) In the compound represented by formula III-2, Ar is phenyl; R1 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (31) Among the compounds represented by formula I, the compounds represented by formula I-0, the compounds represented by formula II-0 or the compounds represented by formula II-1, R2 and R4 are phenyl groups; R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or (32) In the compound represented by formula III-2, Ar is phenyl; R3 is selected from methyl, -CH(CH3)2, -CH2CH(CH3)2, cyclohexyl; R1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; and / or The substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2.

5. The compound according to any one of claims 1 to 4, wherein the structure of the compound represented by formula I is selected from the compound represented by formula III-1 or the compound represented by formula III-3: in, R1 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing one F substituent or phenyl containing one methoxy substituent; R3 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted p-terphenyl; the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or R1 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing one F substituent or phenyl containing one methoxy substituent; R3 is unsubstituted phenyl, unsubstituted naphthyl, unsubstituted anthracenyl, unsubstituted biphenyl, unsubstituted triphenylphosphino, unsubstituted quinolyl, unsubstituted diphenyl ether, unsubstituted dibenzo[b,d]thienyl, unsubstituted m-terphenyl, unsubstituted o-terphenyl, unsubstituted p-terphenyl, phenyl containing one F substituent, phenyl containing one or two methoxy substituents, phenyl containing one trifluoromethyl, phenyl containing three methyl groups, phenyl containing one isopropoxy substituent, phenyl containing one thiomethyl substituent, naphthyl containing one methoxy substituent, or phenyl containing one -SiH(CH3)2 substituent; or R3 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing one F substituent or phenyl containing one methoxy substituent; R1 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenylphosphino, substituted or unsubstituted quinolyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted dibenzo[b,d]thienyl, substituted or unsubstituted terphenyl, substituted or unsubstituted terphenyl or substituted or unsubstituted terphenyl; the substitution is that one or more hydrogen atoms are independently replaced by methyl, methoxy, halogen, phenyl, trifluoromethyl, isopropoxy, phenoxy, diphenylphosphino, thiomethyl or -SiH(CH3)2; or R3 is methyl, -CH(CH3)2, cyclohexyl, unsubstituted phenyl, phenyl containing one F substituent or phenyl containing one methoxy substituent; R1 is unsubstituted phenyl, unsubstituted naphthyl, unsubstituted anthracenyl, unsubstituted biphenyl, unsubstituted triphenylphosphino, unsubstituted quinolyl, unsubstituted diphenyl ether, unsubstituted dibenzo[b,d]thienyl, unsubstituted m-terphenyl, unsubstituted o-terphenyl, unsubstituted p-terphenyl, phenyl containing one F substituent, phenyl containing one or two methoxy substituents, phenyl containing one trifluoromethyl, phenyl containing three methyl groups, phenyl containing one isopropoxy substituent, phenyl containing one thiomethyl substituent, naphthyl containing one methoxy substituent, or phenyl containing one -SiH(CH3)2 substituent; or In the compound represented by formula III-1 or III-3, R1 is a phenyl group containing a methoxy substituent; R3 is a Phenyl substituted with SiH(CH3)2.

6. The compound according to any one of claims 1 to 5, characterized in that The compound represented by formula I is selected from:

7. A method for preparing the compound of formula I according to any one of claims 1 to 6, characterized in that: include: Under an inert gas atmosphere, the compound represented by formula V-1, the compound represented by formula VII-1 and a lithiation agent undergo a first reaction in a solvent to obtain a compound represented by formula VI-1, and then undergo a second reaction with a compound represented by formula IV or a compound represented by formula VIII, and optionally, the compound is mixed with borane under an inert gas atmosphere and stirred for reaction, and then mixed with DABCO to remove borane, and post-treated to obtain a compound represented by formula I; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula I according to any one of claims 1 to 6; or The compound represented by formula I is selected from the compound represented by formula II-0, and the method comprises: Under an inert gas atmosphere, the compound represented by formula V-2, the compound represented by formula VII-1 and the lithiation agent undergo a third reaction in a solvent to obtain a compound represented by formula VI-2, which is then reacted with the compound represented by formula IV or the compound represented by formula VIII for a fourth reaction, and optionally mixed with borane under an inert gas atmosphere and stirred for reaction, and then mixed with DABCO to remove borane, and post-treated to obtain a compound represented by formula II-0; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by II-0 as described in any one of claims 1 to 6; or The compound represented by formula I is selected from the compound represented by formula I-0, and the method comprises: Under an inert gas atmosphere, the compound represented by formula V-3, the compound represented by formula VII-1 and a lithiation agent undergo a fifth reaction in a solvent to obtain a compound represented by formula VI-3, which is then reacted with a compound represented by formula IV or a compound represented by formula VIII for a sixth reaction, and optionally mixed with borane under an inert gas atmosphere and stirred for reaction, and then mixed with DABCO to remove borane, and post-treated to obtain a compound represented by formula I-0; the selection of R1, R2, R3, and R4 are respectively as shown in R1, R2, R3, and R4 in the compound represented by formula I-0 as described in any one of claims 1 to 6; or The compound represented by formula I is selected from the compound represented by formula II-1, and the method comprises: Under an inert gas atmosphere, the compound represented by formula V-4, the compound represented by formula VII-1 and a lithiation agent undergo a seventh reaction in a solvent to obtain a compound represented by formula VI-4, which then undergoes an eighth reaction with the compound represented by formula IV or the compound represented by formula VIII. Optionally, the compound is mixed with borane under an inert gas atmosphere and stirred for reaction, and then mixed with DABCO to remove borane. After post-treatment, a compound represented by formula II-1 is obtained; the selection of R1, R2, R3, and R4 is respectively as shown in R1, R2, R3, and R4 in the compound represented by formula II-1 as described in any one of claims 1 to 6.

8. The method according to claim 7, The solvent comprises tetrahydrofuran, preferably, the solvent is tetrahydrofuran and diethyl ether; and / or The solvent is tetrahydrofuran and diethyl ether, and the volume ratio of tetrahydrofuran to diethyl ether is 1:2-2:1, preferably 1:1; and / or The stirring temperature is 10°C-40°C or 15°C-35°C; and / or The stirring time is 5-20 hours, 10-20 hours or 10-15 hours; and / or The inert gas is at least one of nitrogen, helium, neon, argon, krypton and xenon; and / or The lithiation agent is at least one of n-butyl lithium, sec-butyl lithium or tert-butyl lithium; and / or The compound represented by formula VIII includes at least one of quinolin-8-yllithiu (8-lithium quinolinyl), (2-(diphenylphosphaneyl)phenyl)lithium (2-(diphenylphosphine)phenyl)lithium); and / or The post-treatment includes concentration, purification and drying; and / or The reaction temperature of the first reaction is -84°C to -78°C, preferably -84°C; and / or The reaction temperature of the second reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C; and / or The molar ratio of the compound represented by formula V-1 to the compound represented by formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0; and / or The molar ratio of the compound represented by formula V-1 to the lithiation reagent is 1.0:0.5-1.0:2.0 or 1.0:1.1; and / or The molar ratio of the compound represented by formula V-1 to the compound represented by formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0; and / or The molar ratio of the compound represented by formula V-1 to the compound represented by formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5; and / or 0.1 mmol-1.0 mmol or 0.2 mmol of the compound represented by formula V-1 is added per 1 mL of the solvent; and / or The molar ratio of the compound represented by formula V-1 to borane is 1:1-1:10 or 1:4; and / or The molar ratio of the compound represented by formula V-1 to DABCO is 1:1-1:10 or 1:6; and / or The reaction temperature of the third reaction is -84°C to -78°C, preferably -84°C; and / or The reaction temperature of the fourth reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C; and / or The molar ratio of the compound represented by formula V-2 to the compound represented by formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0; and / or The molar ratio of the compound represented by formula V-2 to the lithiation reagent is 1.0:0.5-1.0:2.0 or 1.0:1.1; and / or The molar ratio of the compound represented by formula V-2 to the compound represented by formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0; and / or The molar ratio of the compound represented by formula V-2 to the compound represented by formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5; and / or 0.1 mmol-1.0 mmol or 0.2 mmol of the compound represented by formula V-2 is added per 1 mL of the solvent; and / or The molar ratio of the compound represented by formula V-2 to borane tetrahydrofuran is 1:1-1:10 or 1:4; and / or The molar ratio of the compound represented by formula V-2 to DABCO is 1:1-1:10 or 1:6; and / or The reaction temperature of the fifth reaction is -84°C to -78°C, preferably -84°C; and / or The reaction temperature of the sixth reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C; and / or The molar ratio of the compound represented by formula V-3 to the compound represented by formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0; and / or The molar ratio of the compound represented by formula V-3 to the lithiation reagent is 1.0:0.5-1.0:2.0 or 1.0:1.1; and / or The molar ratio of the compound represented by formula V-3 to the compound represented by formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0; and / or The molar ratio of the compound represented by formula V-3 to the compound represented by formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5; and / or 0.1 mmol-1.0 mmol or 0.2 mmol of the compound represented by formula V-3 is added per 1 mL of the solvent; and / or The molar ratio of the compound represented by formula V-3 to borane is 1:1-1:10 or 1:4; and / or The molar ratio of the compound represented by formula V-3 to DABCO is 1:1-1:10 or 1:6; and / or The reaction temperature of the seventh reaction is -84°C to -78°C, preferably -84°C; and / or The reaction temperature of the eighth reaction is -116°C to 40°C, -116°C to 30°C, -116°C to 25°C, -116°C to 20°C, -116°C to 15°C or -116°C to -78°C; and / or The molar ratio of the compound represented by formula V-4 to the compound represented by formula VII-1 is 1.0:1.0 to 1.0:3.0, preferably 1.0:1.5 to 1.0:3.0 or 1.0:2.0 to 1.0:3.0; and / or The molar ratio of the compound represented by formula V-4 to the lithiation reagent is 1.0:0.5-1.0:2.0 or 1.0:1.1; and / or The molar ratio of the compound represented by formula V-4 to the compound represented by formula IV is 1.0:1.0 to 1.0:4.0, preferably 1.0:3.0 to 1.0:4.0 or 1.0:3.5 to 1.0:4.0; and / or The molar ratio of the compound represented by formula V-4 to the compound represented by formula VIII is 1.0:1.0-1.0:5.0 or 1.0:2.0 or 1.0:3.5; and / or 0.1 mmol-1.0 mmol or 0.2 mmol of the compound represented by formula V-4 is added per 1 mL of the solvent; and / or The molar ratio of the compound represented by formula V-4 to borane is 1:1-1:10 or 1:4; and / or The molar ratio of the compound represented by formula V-4 to DABCO is 1:1-1:10 or 1:

6.

9. Use of the compound of formula I according to any one of claims 1 to 6 or the compound of formula I obtained by the preparation method according to any one of claims 7 to 8 in asymmetric catalytic reactions or material chemistry; Optionally, the obtained compound represented by formula I is used as a chiral ligand or chiral silicon cation in an asymmetric catalytic reaction or as a functionalized organosilicon or organophosphorus compound in material chemistry.

10. A compound comprising: in R1, R2, and R4 are selected as R1, R2, and R4 in the compound of formula I according to any one of claims 1 to 6; or include

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