Axial chiral thioimine compound as well as preparation method and application thereof

Abstract

The invention discloses an axially chiral thioimine compound and a preparation method and application thereof.The preparation method comprises the steps that sulfenamide, cyclic diaryl iodonium salt, copper tetraacetonitrile hexafluorophosphate, metal center chiral cobalt (III) complex anions, lithium acetate and dichloromethane react for 36 hours at the temperature of minus 10 DEG C under the protection of nitrogen, and the axially chiral thioimine compound is obtained. The axially chiral thioimine compound is obtained through separation and purification; the axial chiral sulfur imine compound prepared by the invention has a potential application of being used as a novel chiral ligand precursor, and can realize efficient synthesis of a series of axial chiral sulfur ligands.

Description

Technical Field

[0001] The present invention relates to an axially chiral sulfilimine compound, and in particular to an axially chiral sulfilimine compound and a preparation method and application thereof. Background Art

[0002] Since the discovery of the first synthetic antibacterial sulfonamide drug, Plutocil, in the 1930s, achiral sulfur-containing functionalities including sulfonamides, sulfonyls, thiols and thioethers have been playing an important role in drug development. However, due to the various oxidation states of sulfur, it can form structurally diverse S(IV) and S(VI) chiral compounds, including sulfoxides, sulfimines, and sulfenamides. In recent years, some studies have shown that these chiral sulfur centers can significantly enhance the structural diversity and complexity of sulfonamide and sulfonyl molecules, which is of great significance for the research and development of drug molecules and the design of chiral catalysts and ligands.

[0003] Among the many chiral sulfur compounds, chiral sulfilimines and their derivatives play an important role in the fields of medicine and pesticides. Their unique structural characteristics often bring about diverse pharmacological properties. Some studies in recent years have shown that their chiral sulfur atoms can enhance the efficacy and safety of drugs, making them indispensable in drug discovery and development. In addition, chiral sulfilimines also have the potential to be used as efficient chiral ligands in transition metal catalytic reactions (Chirality, 2000, 12, 299; Tetrahedron Lett. 2004, 45, 2915; J. Org. Chem. 2019, 84, 7618). Compared with chiral sulfoxides, chiral sulfilimines provide an additional modifiable site, which is of great significance for regulating the chiral environment of the ligand and designing more efficient chiral ligands.

[0004] The asymmetric catalytic synthesis of chiral sulfilimines has always been a research difficulty in the field of asymmetric catalysis. In recent years, the sulfur functionalization reaction of sulfenamides has gradually attracted the interest of chemists at home and abroad, providing a new synthesis idea for sulfenamide compounds (J.Am.Chem.Soc.2023,145,6310; Org.Lett.2023,25,2830; J.Org.Chem.2023,88,16116.). However, due to the strong coordination of sulfur atoms, it is difficult to achieve asymmetric sulfur functionalization of sulfenamides by introducing chiral ligands. Therefore, the development of new catalytic strategies is very necessary for the synthesis of chiral sulfilimines, especially sulfilimines with complex structures and containing multiple chiral elements, which is expected to promote the creation of chiral sulfilimine pesticides and drugs. Summary of the invention

[0005] The purpose of the present invention is to provide an axially chiral sulfilimine compound and a preparation method and application thereof, so as to fill the gap in the prior art and meet the needs of the relevant fields.

[0006] In order to achieve the above object, the present invention provides an axially chiral sulfilimine compound, the general structural formula of the axially chiral sulfilimine compound is:

[0007]

[0008] Among them, R 1 C 1-6 Straight chain or branched alkyl / cycloalkyl, C 6-10 One of aryl or substituted aryl, naphthyl, furyl, thienyl, indolyl and anilino;

[0009] The substituted aryl group is C 1-6 Alkyl substituted aryl, C 1-3 One of an aryl group substituted with an oxyalkyl group, an aryl group substituted with a nitro group, an aryl group substituted with a trifluoromethyl group, an aryl group substituted with a cyano group, or a halogenated aryl group;

[0010] R 2 C 4-7 Straight or branched alkyl, cyclohexyl, C 6-10 One of aryl or substituted aryl, naphthyl, thienyl, and substituted benzyl;

[0011] R 3 and R 4 Each of them is one of hydrogen, alkyl and halogen;

[0012] R 5 and R 6 Each of them is one of hydrogen, alkyl and trifluoromethyl.

[0013] In a preferred embodiment of the present invention, the alkyl group is one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl or isooctyl.

[0014] In a preferred embodiment of the present invention, the cycloalkyl group is one of cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0015] In a preferred embodiment of the present invention, the halogen is one of fluorine, chlorine, bromine or iodine.

[0016] The present invention also provides a method for preparing an axially chiral sulfilimine compound, the preparation method comprising:

[0017] 1) Add sulfenamide, cyclic diaryliodonium salt, tetraethylcyanocopper hexafluorophosphate, metal-centered chiral cobalt (III) complex anion, and lithium acetate into a dry Schlenk tube;

[0018] 2) Evacuate and fill with nitrogen three times, and finally refill the Schlenk tube with nitrogen;

[0019] 3) pre-cooled dichloromethane was added into the reaction tube, and the whole system was reacted at -10°C for 36 hours, and the axial chiral sulfilimine compound was obtained by separation and purification;

[0020]

[0021] The preparation method of the above-mentioned axially chiral azaspirocyclic compounds is to realize the asymmetric S-arylation reaction of sulfonamides by co-catalysis of copper / chiral cobalt (III) coordinated anion sodium salt. The method is applicable to a series of sulfonamides and cyclic diaryl iodonium salts, and can produce multi-chiral sulfilimine compounds with extremely high enantioselectivity, diastereoselectivity, regioselectivity and chemoselectivity.

[0022] In a preferred embodiment of the present invention, relative to 0.15 mmol of sulfenamide, the amount of cyclic diaryliodonium salt is 0.10 mmol, the amount of metal-centered chiral cobalt (III) complex anion is 0.01 mmol, the amount of tetraethylcyanocopper hexafluorophosphate is 0.01 mmol, the amount of lithium acetate is 0.40 mmol, and the amount of dichloromethane is 3.0 mL.

[0023] In the above method, the metal-centered chiral cobalt (III) complex anion catalyst can be prepared by the method reported in the literature (Angew. Chem. Int. Ed. 2015, 54, 11209; Angew. Chem. Int. Ed. 2017, 56, 11931; ZL201510426983.X). In the above reaction, the enantiomeric excess percentage (ee) of the obtained axial chiral sulfilimine compound can reach up to 98%.

[0024] The method for preparing axially chiral sulfilimine compounds of the present invention is to obtain axially chiral sulfilimine compounds by asymmetric S-arylation reaction involving sulfenamide catalyzed by copper and metal-centered chiral cobalt (III) coordinated anions. The method is simple to operate, mild reaction conditions, economical and readily available raw materials, and the prepared product has high optical purity (ee value up to 98%). The axially chiral sulfilimine compounds prepared by the present invention are expected to be widely used in asymmetric synthesis and research and development fields such as medicine and pesticides.

[0025] Other features and advantages of the present invention will be described in detail in the following detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] The accompanying drawings are used to provide a further understanding of the present invention and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present invention but do not constitute a limitation of the present invention. In the accompanying drawings:

[0027] Figure 1 This is the crystal diffraction structure of compound 4a obtained in Example 1. DETAILED DESCRIPTION

[0028] The specific embodiments of the present invention are described in detail below. It should be understood that the specific embodiments described herein are only used to illustrate and explain the present invention and are not intended to limit the present invention. In the examples, the yield of the reaction refers to the isolated yield, and ee refers to the percentage of enantiomeric excess of the reaction.

[0029] The reagents used in the examples, unless otherwise specified, were purchased from Anaiji, Aladdin, and Shanghai National Pharmaceutical Company. The solvents used in the examples, unless otherwise specified, were purchased from Youput Co., Ltd. The thin layer chromatography silica gel used in the examples, unless otherwise specified, was purchased from Qingdao Ocean Chemical Company.

[0030] Example 1: Synthesis and characterization of compound 4a

[0031]

[0032] Step 1: At room temperature, add cyclic diaryliodonium salt 3a (0.10 mmol), sulfenamide 2a (0.15 mmol), tetraethylcyanocopper hexafluorophosphate (0.01 mmol), and metal-centered chiral cobalt (III) complex anion Λ-(S,S)-1a (0.01 mmol) to a 10 mL dry reaction tube; evacuate, fill with nitrogen for three cycles, and finally refill the Schlenk reaction tube with nitrogen; add pre-cooled dichloromethane (3.0 mL) to the reaction tube, and the whole system reacts at -10°C for 36 hours. The obtained mixture is first filtered to remove the solid part, the solid part is washed with dichloromethane, the liquid is combined, washed with water, and the organic phase is dried with anhydrous sodium sulfate. The obtained mixture was first filtered, then concentrated by vacuum distillation, and then dissolved and diluted with 1.0 mL of dichloromethane. Thin layer chromatography silica gel was added to an ordinary glass column, and the above dissolved mixture was subjected to nitrogen pressure column chromatography (column length 15 cm, flow rate 3 drops / second), and the eluent was petroleum ether: ethyl acetate = 10:1-3:1 (volume ratio). It was directly purified by rapid column chromatography, and finally the axial chiral sulfimide compound 4a was isolated with a yield of 96%, ee = 91%, and dr = 98:2. Its absolute configuration was determined by single crystal X-ray diffraction of the recrystallized crystal (ee>99%) (measured at 120K using the Gemimi SUltra four-circle single crystal diffractometer of Oxford Diffraction Company) as ( SThe absolute configurations of compounds 4a-4bd in the following examples are similar. Axial chiral sulfilimine compounds are obtained by separation and purification.

[0033] The structure of compound 4a is as follows:

[0034]

[0035] Characterization data of compound 4a:

[0036] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)benzamide(4a):yield:56.4mg(96%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; whitefoam; [α] D 20 =19.1 (c 0.10 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.55(d,J=7.5Hz,1H),8.24(d,J=6.8Hz,2H),7.90(d ,J=7.3Hz,1H),7.61(t,J=7.4Hz,1H),7.48(d,J=7.0Hz,1H),7.45-7.39(m,1 H),7.39-7.32(m,2H),7.29(d,J=7.7Hz,2H),7.20(d,J=7.6Hz,2H),7.06(t, J=7.4Hz,1H),7.00(d,J=7.0Hz,1H),1.94(s,3H),1.25(s,9H),1.00(s,3H); 13 C-NMR (151MHz, CDCl3) δ175.9,155.8,143.1,139.8,139.7,137.9,137.5,136.9,133.6,133.4,132.6,130.6, 130.4,130.0,129.5,129.4,129.0,127.7,126.3,124.9,101.9,35.1,31.2,19.8,19.3; HRMS(ESI)calculated for C 31 H 31 INOS[M+H] +:592.1171, found: 592.1173; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =7.64min(major),t R =12.05min(minor).

[0037] Example 2: Synthesis and characterization of compound 4b

[0038] The same method as in Example 1 was used, wherein the substrate used was S-4-isopropylphenylsulfenamide. Finally, the product 4b was isolated with a yield of 99%, ee=90%, and dr=98:2.

[0039] The structure of compound 4b is as follows:

[0040]

[0041] Characterization data of compound 4b:

[0042] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(4-isopropylphenyl)-λ 4 -sulfaneyliden-e)benzamide(4b):yield:57.7mg(99%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; whitefoam; [α] D 20 =9.8 (c 0.15 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.53(d,J=8.0Hz,1H),8.23(d,J=7.7Hz,2H),7.89(d,J=7.8 Hz,1H),7.60(t,J=7.7Hz,1H),7.47(d,J=7.5Hz,1H),7.42-7.38(m,1H),7.35(t,J=7 .3Hz,2H),7.19(d,J=7.5Hz,2H),7.12(d,J=7.8Hz,2H),7.05(t,J=7.6Hz,1H),7.00( d,J=7.5Hz,1H),2.88-2.82(m,1H),1.93(s,3H),1.17(d,J=6.8Hz,6H),1.01(s,3H); 13 C-NMR (151MHz, CDCl3) δ175.8,153.5,143.1,139.7,137.9,137.5,137.1,133.7,133.4,133.1,130.6,130.4, 130.1,129.8,129.4,129.0,127.7,127.4,125.0,101.9,34.2,23.8,23.8,19.9,19.3; HRMS(ESI)calculated for C 30 H 29 INOS[M+H] + :578.1015, found: 578.1026; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =15.75min(major),t R =24.77min(minor).

[0043] Example 3: Synthesis and characterization of compound 4c

[0044] The same method as in Example 1 was used, wherein the substrate used was S-4-methylphenylsulfenamide. Finally, the product 4c was isolated with a yield of 98%, ee=90%, and dr>98:2.

[0045] The structure of compound 4c is as follows:

[0046]

[0047] Characterization data of compound 4c:

[0048] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(p-tolyl)-λ 4 -sulfaneylide ne)benzamide(4c):yield:54.0mg(98%),>98:2dr;flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1;white foam;[α] D 20 =14.4(c 0.34CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.53(d,J=8.0Hz,1H),8.23(d,J=7.1Hz,2H),7.90(d,J=7.4Hz,1H),7.61(t,J=7.8Hz,1H),7.48(d,J=7.6Hz,1H),7.40(t,J=7.2Hz,1H),7.35(t,J=7.4Hz,2H),7.17(d,J=8.2Hz,2H),7.11-7.00(m,4H),2.31(s,3H),1.94(s,3H),1.07(s,3H); 13 C-NMR(151MHz,acetone-d6)δ175.2,144.1,143.7,140.8,138.6,138.5,138.2,134.8,134.6,134.4,131.5,131.3,131.1,130.7,130.4,130.1,129.5,128.4,126.5,101.9,21.4,20.3,19.3;HRMS(ESI)calculated for C 28 H 25 INOS[M+H] + :550.0702,found:550.0703;Enantiomeric excess:90%,determined by HPLC(DaicelChiralpak IC,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =19.14min(major),t R =31.73min(minor).

[0049] Example 4: Synthesis and characterization of compound 4d

[0050] The same method as in Example 1 was used, wherein the substrate used was S-phenylsulfenamide. Finally, the product 4d was isolated with a yield of 84%, ee=88%, and dr=97:3.

[0051] The structure of compound 4d is as follows:

[0052]

[0053] Characterization data of compound 4d:

[0054] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(phenyl)-λ 4 -sulfaneylid ene) benzamide (4d): yield: 45.0mg (84%), 97:3dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =36.3 (c 0.45 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.55(d,J=8.0Hz,1H),8.23(d,J=7.6Hz,2H),7.90(d,J=7.7Hz,1H),7.62(t,J=7.8Hz,1H),7.49(d, J=7.6Hz,1H),7.42-7.34(m,4H),7.31-7.25(m,4H),7.06(t,J=7.6Hz,1H),7.02(d,J=7.5Hz,1H),1.94(s,3H),1.04(s,3H); 13 C-NMR (151MHz, CDCl3) δ175.9,143.3,139.7,138.0,137.6,136.9,136.3,133.6,133.4,132.0,130. 7,130.5,130.1,129.7,129.5,129.3,129.0,127.8,125.2,101.8,19.9,19.3; HRMS(ESI)calculated for C 27 H 23 INOS[M+H] +:536.0545, found: 536.0548; Enantiomeric excess: 88%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.54min(major),t R =14.08min(minor).

[0055] Example 5: Synthesis and characterization of compound 4e

[0056] The same method as in Example 1 was used, wherein the substrate used was S-4-methoxyphenylsulfenamide. Finally, the product 4e was isolated with a yield of 95%, ee=90%, and dr>98:2.

[0057] The structure of compound 4e is as follows:

[0058]

[0059] Characterization data of compound 4e:

[0060] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(4-methoxyphenyl)-λ 4 -sulfaneyliden-e)benzamide(4e):yield:53.7mg(95%),>98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=3:1; whitefoam; [α] D 20 = -5.5 (c 0.24CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.54(d,J=8.0Hz,1H),8.23(d,J=7.4Hz,2H),7.90(d,J=7.1Hz,1H),7.61(t,J=7.8Hz,1H),7.48(d,J=7.5Hz,1H),7.40( t,J=7.0Hz,1H),7.35(t,J=7.3Hz,2H),7.20(d,J=8.4Hz,2H),7.09-7.0 1(m,2H),6.77(d,J=8.4Hz,2H),3.76(s,3H),1.94(s,3H),1.10(s,3H); 13 C-NMR (151MHz, CDCl3) δ175.7,162.5,143.1,139.8,139.6,137.9,137.5,137.0,133.7,133.4,131.5,130. 6,130.4,130.0,129.4,128.9,127.7,126.9,124.8,114.7,101.8,55.7,20.1,19.3; HRMS(ESI)calculated for C 28 H 25 INO2[M+H] + :566.0651, found:566.0657; Enantiomericexcess:90%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =19.31min(major),t R =34.61min(minor).

[0061] Example 6: Synthesis and characterization of compound 4f

[0062] The same method as in Example 1 was used, wherein the substrate used was S-4-fluorophenylsulfenamide. Finally, the product 4f was isolated with a yield of 86%, ee=87%, and dr=98:2.

[0063] The structure of compound 4f is as follows:

[0064]

[0065] Characterization data of compound 4f:

[0066] N-((S)-(4-fluorophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulf aneylidene)benz-amide(4f):yield:47.6mg(86%),98:2dr;flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1;white foam;[α] D 20 =31.2(c 0.44CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.56(d,J=7.8Hz,1H),8.22(d,J=7.3Hz,2H),7.91(d,J=7.1Hz,1H),7.63(t,J=7.7Hz,1H),7.51(d,J=7.3Hz,1H),7.45-7.39(m,1H),7.36(t,J=7.1Hz,2H),7.32-7.26(m,2H),7.11-7.02(m,2H),6.97(t,J=8.1Hz,2H),1.95(s,3H),1.11(s,3H); 13 C-NMR(151MHz,CDCl3)δ176.0,164.6(d,J=254.2Hz),143.1,139.6,139.5,138.1,137.7,136.7,133.8,133.1,132.0(d,J=9.2Hz),131.9(d,J=3.1Hz),130.8,130.6,130.1,129.6,128.9,127.8,125.0,116.6(d,J=22.6Hz),101.9,20.1,19.3; 19 F NMR(564MHz,CDCl3)δ-105.53;HRMS(ESI)calculated for C 27 H 22 FINOS[M+H] + :554.0451,found:554.0451;Enantiomeric excess:87%,determined by HPLC(Daicel Chiralpak IC,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):t R=11.63min(major),t R =19.50min(minor).

[0067] Example 7: Synthesis and characterization of compound 4g

[0068] The same method as in Example 1 was used, wherein the substrate used was S-4-chlorophenylsulfenamide. Finally, 4 g of the product was isolated with a yield of 79%, ee=87%, and dr=96:4.

[0069] The structure of compound 4g is as follows:

[0070]

[0071] Characterization data of compound 4g:

[0072] N-((S)-(4-chlorophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sul faneylidene)benz-amide(4g):yield:45.0mg(79%),96:4dr; flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =7.1 (c 0.21 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.55(d,J=8.0Hz,1H),8.21(d,J=7.6Hz,2H),7.90(d,J=6.1Hz,1H),7.63(t,J=7.8Hz,1H),7.50(d,J=7.5Hz,1H) ,7.41(t,J=7.0Hz,1H),7.36(t,J=7.3Hz,2H),7.25(d,J=8.0Hz,2H),7.21(d,J=8.3Hz,2H),7.11-7.01(m,2H),1.95(s,3H),1.13(s,3H); 13C-NMR (151MHz, CDCl3) δ176.0,143.2,139.6,139.5,138.4,138.1,137.7,136.6,134.9,133.9,132. 8,130.9,130.7,130.2,129.6,129.5,129.0,127.8,125.2,101.8,20.1,19.3; HRMS(ESI)calculated for C 27 H 22 ClINOS[M+H] + :570.0155, found: 570.0159; Enantiomeric excess: 87%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =12.89min(major),t R =20.96min(minor).

[0073] Example 8: Synthesis and characterization of compound 4h

[0074] The same method as in Example 1 was used, wherein the substrate used was S-4-bromophenylsulfenamide. Finally, the product 4h was isolated with a yield of 72%, ee=85%, and dr=90:10.

[0075] The structure of compound 4h is as follows:

[0076]

[0077] Characterization data of compound 4h:

[0078] N-((S)-(4-bromophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sul faneylidene) ben-zamide (4h): yield: 44.1mg (72%), 90:10dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 = -10.5 (c 0.44 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.55(d,J=8.0Hz,1H),8.21(d,J=7.5Hz,2H),7.95-7.85(m,1H),7.63(t,J=7.8Hz,1H),7.51(d,J= 7.7Hz,1H),7.47-7.39(m,3H),7.37(t,J=7.4Hz,2H),7.15(d,J=8.4Hz,2H),7.10-7.02(m,2H),1.95(s,3H),1.14(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.0,143.3,139.7,139.5,138.2,137.7,136.7,135.7,133.9,132.5,131. 0,130.8,130.7,130.2,129.6,129.0,127.8,126.7,125.3,101.8,20.1,19.3; HRMS(ESI)calculated for C 27 H 22 BrINOS[M+H] + :613.9650, found:613.9657; Enantiomeric excess: 85%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =8.60min(major),t R =13.58min(minor).

[0079] Example 9: Synthesis and characterization of compound 4i

[0080] The same method as in Example 1 was used, wherein the substrate used was S-4-trifluoromethylphenylsulfenamide. Finally, the product 4i was isolated with a yield of 86%, ee=83%, and dr=91:9.

[0081] The structure of compound 4i is as follows:

[0082]

[0083] Characterization data of compound 4i:

[0084] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(4-(trifluoromethyl)phe nyl)-λ 4 -sulfaneyl-idene)benzamide(4i):yield:52.0mg(86%),91:9dr;flash column chromatography eluent,petroleum ether / ethylacetate=5:1;white foam;[α] D 20 =17.0(c 0.22CH2Cl2); 1 H-NMR(400MHz,CDCl3)δ8.61(d,J=7.9Hz,1H),8.25-8.19(m,2H),7.92(d,J=6.7Hz,1H),7.66(t,J=7.8Hz,1H),7.57-7.52(m,3H),7.44-7.35(m,5H),7.13-7.05(m,2H),1.96(s,3H),1.07(s,3H); 13 C-NMR(101MHz,CDCl3)δ176.2,143.3,140.8,139.5,139.4,138.3,137.8,136.3,134.1,133.7(q,J=32.8Hz),132.3,131.0,130.8,130.2,129.9,129.8,129.0,127.9,126.2(q,J=3.6Hz),125.5,123.3(q,J=272.9Hz),101.9,20.0,19.3; 19 F NMR(376MHz,CDCl3)δ-63.12;HRMS(ESI)calculated for C 28 H 22 F3INOS[M+H] + :604.0419,found:604.0426;Enantiomericexcess:83%,determined by HPLC(Daicel Chiralpak IC,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =7.47min(major),t R =10.76min(minor).

[0085] Example 10: Synthesis and characterization of compound 4j

[0086] The same method as in Example 1 was used, wherein the substrate used was S-3-methylphenylsulfenamide. Finally, the product 4j was isolated with a yield of 99%, ee=90%, and dr=98:2.

[0087] The structure of compound 4j is as follows:

[0088]

[0089] Characterization data of compound 4j:

[0090] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(m-tolyl)-λ 4 -sulfaneylid ene) benzamide (4j): yield: 54.5mg (99%), 98:2dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =16.7 (c 0.25 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.54(d,J=8.0Hz,1H),8.24(d,J=7.4Hz,2H),7.91(d,J=7.7Hz,1H),7.61(t,J=7.8Hz,1H),7.48(d,J=7.5Hz,1H),7.41(t,J=7 .1Hz,1H),7.36(t,J=7.3Hz,2H),7.23-7.11(m,3H),7.07(t,J=7.7Hz,1H), 7.02(d,J=7.5Hz,1H),6.97(s,1H),2.25(s,3H),1.94(s,3H),1.05(s,3H); 13C-NMR (151MHz, CDCl3) δ175.9,143.1,139.9,139.7,139.1,137.9,137.6,136.9,135.8,133.5,133.5,132.8,130. 6,130.4,130.1,129.8,129.5,129.3,129.0,127.8,126.5,125.0,101.8,21.3,20.0,19.3; HRMS(ESI)calculated for C 28 H 25 INOS[M+H] + :550.0702, found: 550.0711; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =19.05min(major),t R =31.80min(minor).

[0091] Example 11: Synthesis and characterization of compound 4k

[0092] The same method as in Example 1 was used, wherein the substrate used was S-3-fluorophenylsulfenamide. Finally, the product 4k was isolated with a yield of 75%, ee=86%, and dr=94:6.

[0093] The structure of compound 4k is as follows:

[0094]

[0095] Characterization data of compound 4k:

[0096] N-((S)-(3-fluorophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulf aneylidene) ben-zamide (4k): yield: 41.4mg (75%), 94:6dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =16.7 (c 0.21 CH2Cl2);1 H-NMR (600MHz, CDCl3) δ8.55(d,J=8.0Hz,1H),8.22(d,J=7.5Hz,2H),7.92(d,J=7.1Hz,1H),7.64(t,J=7.8Hz,1H),7.52(d,J=7.6Hz,1H ),7.43(t,J=7.2Hz,1H),7.37(t,J=7.4Hz,2H),7.29-7.25(m,1H),7.15-7.03(m,4H),7.00(d,J=7.8Hz,1H),1.96(s,3H),1.14(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.1,162.4(d,J=252.2Hz),143.3,139.6,139.6,138.2,137.8,136.6,133.9,130.9,130.8,130.8, 130.7, 130.1, 129.7, 129.0, 127.9, 125.4, 125.3 (d, J = 3.3Hz), 119.3 (d, J = 21.4Hz), 116.6 (d, J = 23.8Hz), 101.8, 20.1, 19.3; 19 F NMR (564MHz, CDCl3) δ-105.32; C 27 H 22 FINOS[M+H] + :554.0451, found: 554.0456; Enantiomeric excess: 86%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =7.48min(major),t R =10.22min(minor).

[0097] Example 12: Synthesis and characterization of compound 41

[0098] The same method as in Example 1 was used, wherein the substrate used was S-3-chlorophenylsulfenamide. Finally, the product 41 was isolated with a yield of 79%, ee=79%, and dr=98:2.

[0099] The structure of compound 41 is as follows:

[0100]

[0101] Characterization data of compound 4l:

[0102] N-((S)-(3-chlorophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)benzamide (4l): yield: 45.0 mg (79%), 98:2 dr; flash column chromatography eluent, petroleum ether / ethyl acetate = 5:1; white foam; [α] D 20 = 27.2 (c 0.47 CH2Cl2); 1 1H-NMR (600 MHz, CDCl3) δ 8.56 (d, J = 7.7 Hz, 1H), 8.23 (d, J = 7.0 Hz, 2H), 7.96 - 7.88 (m, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.51 (d, J = 7.1 Hz, 1H), 7.45 - 7.41 (m, 1H), 7.40 - 7.32 (m, 3H), 7.25 - 7.19 (m, 2H), 7.16 - 7.05 (m, 3H), 1.96 (s, 3H), 1.12 (s, 3H); 13 13C-NMR (151 MHz, CDCl3) δ 176.1, 143.2, 139.6, 139.5, 138.3, 138.2, 137.8, 136.6, 135.0, 133.9, 132.8, 132.1, 130.9, 130.7, 130.5, 130.2, 129.7, 129.5, 129.0, 127.9, 127.3, 125.3, 101.7, 20.1, 19.3; HRMS (ESI) calculated for C 27 H 22 ClINOS [M + H] + : 570.0155, found: 570.0157; Enantiomeric excess: 79%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane = 30 / 70, flow rate = 1.0 mL / min, T = 30 °C, λ = 254 nm): t R = 8.77 min (major), t R = 12.25 min (minor).

[0103] Example 13: Synthesis and characterization of compound 4m

[0104] The same method as in Example 1 was used, wherein the substrate used was S-3-bromophenylsulfenamide. Finally, the product 4m was isolated with a yield of 91%, ee=81%, and dr=98:2.

[0105] The structure of compound 4m is as follows:

[0106]

[0107] Characterization data of compound 4m:

[0108] N-((S)-(3-bromophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sul faneylidene) ben-zamide (4m): yield: 55.8mg (91%), 98:2dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =22.7 (c 0.29 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.56(d,J=7.9Hz,1H),8.23(d,J=7.3Hz,2H),7.92(d,J=5.8Hz,1H),7.64(t,J=7.6Hz,1H),7.51(d,J=7.6Hz,2H),7.43( t,J=6.8Hz,1H),7.38(t,J=7.1Hz,2H),7.30(d,J=7.7Hz,1H),7.22(s,1 H),7.16(t,J=7.7Hz,1H),7.14-7.07(m,2H),1.96(s,3H),1.12(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.1,143.2,139.6,139.4,138.6,138.2,137.8,136.6,135.0,133.9,132.8,132.3,1 30.9,130.8,130.8,130.2,129.7,129.0,127.9,127.7,125.2,122.8,101.7,20.1,19.3; HRMS(ESI)calculated for C 27 H22 BrINOS[M+H] + :613.9650, found: 613.9656; Enantiomeric excess: 81%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =11.25min(major),t R =16.17min(minor).

[0109] Example 14: Synthesis and characterization of compound 4n

[0110] The same method as in Example 1 was used, wherein the substrate used was S-3-trifluoromethylphenylsulfenamide. Finally, the product 4n was isolated with a yield of 56%, ee=80%, and dr=90:10.

[0111] The structure of compound 4n is as follows:

[0112]

[0113] Characterization data of compound 4n:

[0114] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(3-(trifluoromethyl)phe nyl)-λ 4 -sulfaneyl-idene) benzamide (4n): yield: 33.8mg (56%), 90:10dr; flash column chromatography eluent, petroleum ether / ethylacetate=5:1; white foam; [α] D 20 =22.4 (c 0.37 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.60(d,J=8.0Hz,1H),8.22(d,J=7.4Hz,2H),7.93(d,J=7.8Hz,1H),7.70-7.63(m,2H),7.61(d,J=8.0Hz,1H) ,7.53(d,J=7.6Hz,1H),7.47-7.42(m,2H),7.41-7.32(m,3H),7.11(t,J=7.7Hz,1H),7.05(d,J=7.5Hz,1H),1.96(s,3H),1.04(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.2,143.3,139.5,139.3,138.3,138.2,137.9,136.5,134.1,132.4,131.0,130 .8,130.4,130.2,129.8,129.0,128.7(q,J=3.5Hz),127.9,126.7(q,J=3.7Hz),125.3,101.8,19.9,19.3; 19 F NMR(376MHz, CDCl3)δ-62.80; HRMS(ESI)calculated forC 28 H 22 F3INOS[M+H] + :604.0419, found: 604.0423; Enantiomeric excess: 80%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =5.85min(major),t R =7.58min(minor).

[0115] Example 15: Synthesis and characterization of compound 4o

[0116] The same method as in Example 1 was used, wherein the substrate used was S-2-methylphenylsulfenamide. Finally, the product 4o was isolated with a yield of 94%, ee=84%, and dr=98:2.

[0117] The structure of compound 4o is as follows:

[0118]

[0119] Characterization data of compound 4o:

[0120] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(o-tolyl)-λ 4 -sulfaneylide ne)benzamide(4o):yield:51.6mg(94%),98:2dr;flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1;white foam;[α] D 20 =16.1(c 0.52CH3OH); 1 H-NMR(600MHz,CDCl3)δ8.72(d,J=8.0Hz,1H),8.23(d,J=7.5Hz,2H),7.89(d,J=7.0Hz,1H),7.67(t,J=7.8Hz,1H),7.50(d,J=7.5Hz,1H),7.40(t,J=7.9Hz,2H),7.35(t,J=7.4Hz,2H),7.23(t,J=7.4Hz,1H),7.13(t,J=7.6Hz,1H),7.09-6.96(m,3H),1.98(s,3H),1.88(s,3H),0.98(s,3H); 13 C-NMR(151MHz,CDCl3)δ175.6,143.0,141.5,139.9,139.9,138.1,137.6,136.9,135.3,133.5,133.1,131.5,130.6,130.6,130.5,130.3,130.3,129.4,128.9,127.8,127.5,125.8,101.9,19.5,19.3,18.6;HRMS(ESI)calculated for C 28 H 25 INOS[M+H] + :550.0702,found:550.0704;Enantiomericexcess:84%,determined by HPLC(Daicel Chiralpak IC,isopropanol / hexane=10 / 90,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =51.18min(major),t R =46.36min(minor).

[0121] Example 16: Synthesis and characterization of compound 4p

[0122] The same method as in Example 1 was used, wherein the substrate used was S-3,4-difluorophenylsulfenamide. Finally, the product 4p was separated with a yield of 77%, ee=82%, and dr=96:4.

[0123] The structure of compound 4p is as follows:

[0124]

[0125] Characterization data of compound 4p:

[0126] N-((S)-(3,4-difluorophenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)benzamide(4p):yield:44.0mg(77%),96:4dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; whitefoam; [α] D 20 =23.6 (c 0.44 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.56(d,J=8.0Hz,1H),8.21(d,J=8.0Hz,2H),7.92(t,J=4.4Hz,1H),7.65(t,J=7.8Hz,1H) ,7.53(d,J=7.6Hz,1H),7.44(t,J=6.8Hz,1H),7.38(t,J=7.5Hz,2H),7.16-7.00(m,5H),1.97(s,3H),1.20(s,3H); 13C-NMR (151MHz, CDCl3) δ176.2, 152.6 (dd, J=256.7, 12.3Hz), 150.4 (dd, J=2 55.3,13.5Hz),143.3,139.6,139.4,138.3,137.9,136.5,134.1,132.7,13 1.0,130.8,130.1,129.8,129.0,127.9,126.3(d,J=3.8Hz),126.3(d,J=4. 2Hz),125.3,118.8(d,J=19.2Hz),118.2(d,J=18.4Hz),101.9,20.3,19.3; 19 F NMR(376MHz, CDCl3)δ-130.18(d,J=21.1Hz),-133.39(d,J=20.5Hz); HRMS(ESI)calculated for C 27 H 21 F2INOS[M+H] + :572.0357, found: 572.0358; Enantiomeric excess: 82%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =6.58min(major),t R =9.48min(minor).

[0127] Example 17: Synthesis and characterization of compound 4q

[0128] The same method as in Example 1 was used, wherein the substrate used was S-3,5-dimethylphenylsulfenamide. Finally, the product 4q was isolated with a yield of 76%, ee=90%, and dr=95:5.

[0129] The structure of compound 4q is as follows:

[0130]

[0131] Characterization data of compound 4q:

[0132] N-((S)-(3,5-dimethylphenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4-sulfaneyliden-e)benzamide(4q):yield:42.8mg(76%),95:5dr;flash column chromatography eluent,petroleum ether / ethyl acetate=5:1;whitefoam;[α] D 20 =49.3(c 0.43CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.52(d,J=8.0Hz,1H),8.25(d,J=7.9Hz,2H),7.91(d,J=7.8Hz,1H),7.61(t,J=7.8Hz,1H),7.47(d,J=7.6Hz,1H),7.43-7.39(m,1H),7.37(t,J=7.2Hz,2H),7.07(t,J=7.5Hz,1H),7.02(d,J=7.6Hz,1H),6.99(s,1H),6.83(s,2H),2.20(s,6H),1.94(s,3H),1.06(s,3H); 13 C-NMR(151MHz,CDCl3)δ175.8,143.1,140.0,139.8,139.1,137.8,137.6,137.1,135.6,133.7,133.4,130.6,130.3,129.7,129.4,129.0,127.7,127.0,125.0,101.8,21.2,20.0,19.2;HRMS(ESI)calculated for C 29 H 27 INOS[M+H] + :564.0858,found:564.0855;Enantiomeric excess:90%,determined by HPLC(Daicel Chiralpak IF,isopropanol / hexane=10 / 90,flowrate=1.0mL / min,T=30℃,λ=254nm):t R =22.97min(major),t R =45.37min(minor).

[0133] Example 18: Synthesis and characterization of compound 4r

[0134] The same method as in Example 1 was used, wherein the substrate used was S-2-naphthylsulfenamide. Finally, the product 4r was isolated with a yield of 43%, ee=90%, and dr=95:5.

[0135] The structure of compound 4r is as follows:

[0136]

[0137] Characterization data of compound 4r:

[0138] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(naphthalen-2-yl)-λ 4 -su lfaneylidene) ben-zamide (4r): yield: 25.2mg (43%), 95:5dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 = -11.0 (c 0.28 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.60(d,J=8.0Hz,1H),8.26(d,J=7.5Hz,2H),7.97(d, J=7.9Hz,1H),7.80-7.74(m,2H),7.67(d,J=7.8Hz,1H),7.64(t,J=7.9Hz,1H) ,7.58-7.51(m,3H),7.51-7.46(m,2H),7.42(t,J=7.2Hz,1H),7.37(t,J=7.4H z,2H),7.11(t,J=7.7Hz,1H),6.89(d,J=7.6Hz,1H),1.93(s,3H),0.76(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.0,143.3,139.9,139.7,138.0,137.7,136.9,134.6,133.6,133.1,132.3,132.3,131.3,130.7,1 30.4,129.9,129.9,129.5,129.0,128.7,128.6,128.0,127.8,127.4,125.0,123.8,101.9,19.8,19.3; HRMS(ESI)calculated for C 31 H25 INOS[M+H] + :586.0702, found:586.0705; Enantiomeric excess:90%, determined by HPLC (DaicelChiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =22.54min(major),t R =36.43min(minor).

[0139] Example 19: Synthesis and characterization of compound 4s

[0140] The same method as in Example 1 was used, wherein the substrate used was S-2-thienylsulfenamide. Finally, the product 4s was isolated with a yield of 56%, ee=83%, and dr=97:3.

[0141] The structure of compound 4s is as follows:

[0142]

[0143] Characterization data of compound 4s:

[0144] N-((R)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(thiophen-2-yl)-λ 4 -sulfa neylidene)ben-zamide(4s):yield:30.3mg(56%),97:3dr; flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =32.9 (c 0.30CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.52(d,J=8.0Hz,1H),8.23(d,J=7.2Hz,2H),7.90(d,J =7.7Hz,1H),7.61(t,J=7.8Hz,1H),7.55(d,J=5.1Hz,1H),7.51(d,J=7.6Hz,1H) ,7.42(t,J=7.3Hz,1H),7.36(t,J=7.4Hz,2H),7.11(d,J=7.5Hz,1H),7.06(t,J= 7.7Hz,1H),6.95(d,J=3.7Hz,1H),6.91-6.86(m,1H),1.97(s,3H),1.28(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.2,143.2,139.7,139.6,138.1,137.6,136.7,136.2,134.6,134.2,133.9,1 33.6,130.8,130.5,129.8,129.7,129.1,127.8,126.7,124.5,101.7,20.0,19.3; HRMS(ESI)calculated for C 25 H 21 INOS2[M+H] + :542.0109, found: 542.0105; Enantiomeric excess: 83%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.41min(major),t R =16.06min(minor).

[0145] Example 20: Synthesis and characterization of compound 4t

[0146] The same method as in Example 1 was used, wherein the substrate used was S-n-butylsulfenamide. Finally, the product 4t was isolated with a yield of 94%, ee=89%, and dr=97:3.

[0147] The structure of compound 4t is as follows:

[0148]

[0149] Characterization data of compound 4t:

[0150] N-((S)-butyl((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)benzamide(4t):yield:48.4mg(94%),97:3dr;flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1;colorless oil;[α] D 20 =-13.8(c 0.48CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.22(d,J=7.3Hz,2H),8.09(d,J=7.7Hz,1H),7.88(d,J=7.8Hz,1H),7.52(t,J=7.6Hz,1H),7.49(d,J=7.2Hz,1H),7.44-7.39(m,1H),7.37(t,J=7.1Hz,2H),7.31(d,J=7.5Hz,1H),7.06(t,J=7.7Hz,1H),2.97-2.88(m,1H),2.74-2.65(m,1H),2.05(s,3H),2.01(s,3H),1.75-1.66(m,1H),1.47-1.38(m,1H),1.34-1.26(m,1H),1.21-1.13(m,1H),0.79(t,J=7.2Hz,3H); 13 C-NMR(151MHz,CDCl3)δ176.4,142.8,140.2,138.0,137.9,137.8,137.3,133.5,132.3,130.5,130.5,130.2,129.3,129.0,127.8,127.8,125.8,101.8,46.7,24.6,21.5,21.3,19.4,13.6;HRMS(ESI)calculated for C 25 H 27 INOS[M+H] + :516.0858,found:516.0852;Enantiomeric excess:89%,determined by HPLC(Daicel Chiralpak IF,isopropanol / hexane=30 / 70,flowrate=1.0mL / min,T=30℃,λ=254nm):tR =6.68min(major),t R =7.62min(minor).

[0151] Example 21: Synthesis and characterization of compound 4u

[0152] The same method as in Example 1 was used, wherein the substrate used was S-isoamylsulfenamide. Finally, the product 4u was isolated with a yield of 99%, ee=89%, and dr=96:4.

[0153] The structure of compound 4u is as follows:

[0154]

[0155] Characterization data of compound 4u:

[0156] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(isopentyl)-λ 4 -sulfaneyl idene)benzamide(4u):yield:52.4mg(99%),96:4dr; flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1; colorless oil; [α] D 20 = -21.3 (c 0.53 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.22(d,J=7.4Hz,2H),8.07(d,J=7.7Hz,1H),7.88(d,J=7.9Hz,1H),7.52( t,J=7.7Hz,1H),7.49(d,J=7.4Hz,1H),7.42(t,J=7.2Hz,1H),7.37(t,J=7.4Hz,2H),7.31(d,J=7.6 Hz,1H),7.06(t,J=7.8Hz,1H),2.96-2.90(m,1H),2.74-2.67(m,1H),2.06(s,3H),2.01(s,3H),1.6 2-1.57(m,1H),1.54-1.47(m,1H),1.37-1.31(m,1H),0.80(d,J=6.6Hz,3H),0.75(d,J=6.6Hz,3H); 13C-NMR (151MHz, CDCl3) δ176.4,142.8,140.2,138.0,137.9,137.8,137.3,133.5,132.4,130.5,130.5,13 0.2,129.3,129.0,127.8,125.7,101.8,45.2,31.2,27.4,22.4,22.1,21.4,19.5; HRMS(ESI)calculated for C 26 H 29 INOS[M+H] + :530.1015, found: 530.1015; Enantiomeric excess: 89%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.23min(major),t R =7.13min(minor).

[0157] Example 22: Synthesis and Characterization of Compound 4v

[0158] The same method as in Example 1 was used, wherein the substrate used was S-n-heptylsulfenamide. Finally, the product 4v was isolated with a yield of 89%, ee=90%, and dr=97:3.

[0159] The structure of compound 4v is as follows:

[0160]

[0161] Characterization data of compound 4v:

[0162] N-((S)-heptyl((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden e) benzamide (4v): yield: 49.6mg (89%), 97:3dr; flash columnchromatography eluent, petroleum ether / ethyl acetate=5:1; colorless oil; [α] D 20 = -21.0 (c 0.49 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.22(d,J=7.3Hz,2H),8.08(d,J=7.6Hz,1H),7.88(d,J=7.8H z,1H),7.55-7.46(m,2H),7.45-7.40(m,1H),7.37(t,J=7.2Hz,2H),7.31(d,J=7.5Hz, 1H),7.06(t,J=7.7Hz,1H),2.94-2.87(m,1H),2.74-2.67(m,1H),2.05(s,3H),2.02(s ,3H),1.75-1.68(m,1H),1.49-1.42(m,1H),1.25-1.10(m,8H),0.84(t,J=7.1Hz,3H); 13 C-NMR (151MHz, CDCl3) δ176.4,142.7,140.1,138.0,137.9,137.7,137.2,133.5,132.2,130.6,130.4,130.2,1 29.3,129.0,127.8,125.7,101.8,46.8,31.6,28.7,28.2,22.6,22.5,21.3,19.5,14.1; HRMS(ESI)calculated for C 28 H 33 INOS[M+H] + :558.1328, found: 558.1333; Enantiomeric excess: 90%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =6.53min(major),t R =7.92min(minor).

[0163] Example 23: Synthesis and characterization of compound 4w

[0164] The same method as in Example 1 was used, wherein the substrate used was S-cyclohexylsulfenamide. Finally, the product 4w was isolated with a yield of 85%, ee=91%, and dr=96:4.

[0165] The structure of compound 4w is as follows:

[0166]

[0167] Characterization data of compound 4w:

[0168] N-((S)-cyclohexyl((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyli dene)benzamide(4w):yield:46.0mg(85%),96:4dr;flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1;colorless oil;[α] D 20 =-13.7(c 0.51CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.24(d,J=7.4Hz,2H),7.93(d,J=7.1Hz,1H),7.89(d,J=7.9Hz,1H),7.51-7.45(m,2H),7.42(t,J=7.2Hz,1H),7.37(t,J=7.3Hz,2H),7.31(d,J=7.6Hz,1H),7.07(t,J=7.8Hz,1H),2.62-2.56(m,1H),2.07(s,3H),2.02(s,3H),1.89-1.70(m,4H),1.68-1.63(m,1H),1.61-1.57(m,2H),1.20-1.09(m,3H); 13 C-NMR(151MHz,CDCl3)δ176.7,142.9,140.2,138.0,138.0,138.0,137.6,133.3,131.4,130.5,130.4,129.9,129.1,128.9,127.7,126.1,102.0,56.4,29.0,26.5,26.0,25.2,24.2,21.2,19.5;HRMS(ESI)calculated for C 27 H 29 INOS[M+H] + :542.1015,found:542.1021;Enantiomeric excess:91%,determined by HPLC(Daicel Chiralpak IC,isopropanol / hexane=10 / 90,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =49.85min(major),tR =94.26min(minor).

[0169] Example 24: Synthesis and characterization of compound 4x

[0170] The same method as in Example 1 was used, wherein the substrate used was S-benzylsulfenamide. Finally, the product 4x was isolated with a yield of 70%, ee=91%, and dr>98:2.

[0171] The structure of compound 4x is as follows:

[0172]

[0173] Characterization data of compound 4x:

[0174] N-((S)-benzyl((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden e)benzamide(4x):yield:38.4mg(70%),>98:2dr; flash columnchromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =16.9 (c 0.18 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.12(d,J=6.8Hz,2H),7.88(d,J=7.4Hz,1H),7.61(d,J=7.4Hz,1H),7.50(d,J=6.9Hz,1H),7.41(d,J=7.0Hz,2H),7.38-7.29(m ,3H),7.29-7.26(m,1H),7.22-7.13(m,2H),7.10(t,J=7.5Hz,1H),6.85(d, J=6.6Hz,2H),4.50(d,J=12.6Hz,1H),3.89(d,J=12.6Hz,1H),2.04(s,6H); 13C-NMR (151MHz, CDCl3) δ176.7,143.6,140.1,138.0,137.7,137.3,133.9,131.5,131.1,130.6,130.5,1 30.3,129.0,128.9,128.8,128.3,128.2,127.8,127.5,101.9,51.8,21.4,19.6; HRMS(ESI)calculated for C 28 H 25 INOS[M+H] + :550.0702, found: 550.0704; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =11.93min(major),t R =10.61min(minor).

[0175] Example 25: Synthesis and characterization of compound 4y

[0176] The same method as in Example 1 was used, wherein the substrate used was S-4-methylbenzylsulfenamide. Finally, the product 4y was isolated with a yield of 75%, ee=90%, and dr>98:2.

[0177] The structure of compound 4y is as follows:

[0178]

[0179] Characterization data of compound 4y:

[0180] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(4-methylbenzyl)-λ 4 -sul faneylidene)ben-zamide(4y):yield:42.2mg(75%),>98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; whitefoam; [α] D 20 = -18.8 (c 0.19 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.13(d,J=6.7Hz,2H),7.88(d,J=7.4Hz,1H),7.62(d,J=7.4Hz,1H),7.49(d,J=6.8Hz,1H),7.46-7.38(m,2H),7.39-7.27(m ,3H),7.10(t,J=7.4Hz,1H),6.99(d,J=6.8Hz,2H),6.73(d,J=6.7Hz,2H), 4.47(d,J=12.7Hz,1H),3.86(d,J=12.7Hz,1H),2.29(s,3H),2.03(s,6H); 13 C-NMR (151MHz, CDCl3) δ176.6,143.6,140.2,138.7,138.0,137.7,137.6,137.3,133.8,131.4,131.2,130.5, 130.5,130.3,129.0,128.9,128.9,127.8,127.5,125.0,101.9,51.6,21.4,21.3,19.6; HRMS(ESI)calculated for C 29 H 27 INOS[M+H] + :564.0858, found: 564.0855; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =11.87min(major),t R =10.60min(minor).

[0181] Example 26: Synthesis and Characterization of Compound 4z

[0182] The same method as in Example 1 was used, wherein the substrate used was S-4-tert-butylbenzylsulfenamide. Finally, the product 4z was isolated with a yield of 79%, ee=88%, and dr=96:4.

[0183] The structure of compound 4z is as follows:

[0184]

[0185] Characterization data of compound 4z:

[0186] N-((S)-(4-(tert-butyl)benzyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)benzamide(4z):yield:47.8mg(79%),96:4dr;flash column chromatography eluent,petroleum ether / ethyl acetate=5:1;whitefoam;[α] D 20 =-27.5(c 0.43CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.13(d,J=7.2Hz,2H),7.87(d,J=7.9Hz,1H),7.71(d,J=7.9Hz,1H),7.50(d,J=7.5Hz,1H),7.45-7.40(m,2H),7.36(t,J=7.4Hz,2H),7.30(d,J=7.6Hz,1H),7.20(d,J=8.2Hz,2H),7.09(t,J=7.8Hz,1H),6.82(d,J=8.1Hz,2H),4.36(d,J=12.6Hz,1H),4.05(d,J=12.6Hz,1H),2.02(s,3H),1.91(s,3H),1.27(s,9H); 13 C-NMR(151MHz,CDCl3)δ176.7,152.1,143.9,140.3,138.0,137.8,137.7,137.4,133.9,131.7,131.0,130.5,130.5,130.2,129.1,129.0,127.8,127.2,125.6,125.4,101.8,52.3,34.8,31.4,21.2,19.6;HRMS(ESI)calculated for C 32 H 33 INOS[M+H] + :606.1328,found:606.1330;Enantiomeric excess:88%,determined by HPLC(Daicel Chiralpak IC,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):t R=14.72min(major),t R =9.90min(minor).

[0187] Example 27: Synthesis and Characterization of Compound 4aa

[0188] The same method as in Example 1 was used, wherein the substrate used was S-3-methylbenzylsulfenamide. Finally, the product 4aa was isolated with a yield of 86%, ee=87%, and dr=98:2.

[0189] The structure of compound 4aa is as follows:

[0190]

[0191] Characterization data of compound 4aa:

[0192] N-((S)-((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)(3-methylbenzyl)-λ 4 -sul faneylidene)ben-zamide(4aa):yield:50.0mg(88%),>98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; whitefoam; [α] D 20 =7.0 (c 0.28 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.12(d,J=6.2Hz,2H),7.88(d,J=7.1Hz,1H),7.62(d,J=7.1Hz,1H),7.50(d,J=6.0Hz,1H),7.46-7.37(m,2H),7.39-7 .27(m,3H),7.16-6.98(m,3H),6.66(s,1H),6.62(d,J=4.0Hz,1H),4.45(d,J=12.6Hz,1H),3.87(d,J=12.5Hz,1H),2.17(s,3H),2.03(s,6H); 13C-NMR (151MHz, CDCl3) δ176.7,143.6,140.1,138.0,137.9,137.7,137.6,137.3,133.9,132.4,131.2,130.5,130.5, 130.3,129.5,128.9,128.8,128.4,128.1,127.9,127.7,127.5,101.9,51.9,21.3,21.2,19.6; HRMS(ESI)calculated for C 29 H 27 INOS[M+H] + :564.0858, found: 564.0858; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =11.32min(major),t R =10.17min(minor).

[0193] Example 28: Synthesis and Characterization of Compound 4ab

[0194] The same method as in Example 1 was used, wherein the substrate used was N-4-methylphenylcarbonylsulfenamide. Finally, the product 4ab was isolated with a yield of 97%, ee=92%, and dr=98:2.

[0195] The structure of compound 4ab is as follows:

[0196]

[0197] Characterization data of compound 4ab:

[0198] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-4-methylbenzamide(4ab):yield:58.7mg(97%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20=15.1 (c 0.17 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.53(d,J=7.9Hz,1H),8.13(d,J=7.8Hz,2H),7.90( d,J=7.7Hz,1H),7.60(t,J=7.8Hz,1H),7.47(d,J=7.5Hz,1H),7.28(d,J=8.3 Hz,2H),7.19(d,J=8.3Hz,2H),7.16(d,J=7.8Hz,2H),7.05(t,J=7.7Hz,1H) ,6.99(d,J=7.5Hz,1H),2.36(s,3H),1.93(s,3H),1.25(s,9H),0.99(s,3H); 13 C-NMR (151MHz, CDCl3) δ176.0,155.7,143.1,140.7,139.8,139.8,137.9,137.6,134.4,133.9,133.4,132.8,130 .4,130.0,129.5,129.4,129.0,128.4,126.3,125.0,101.9,35.1,31.2,21.6,19.9,19.3; HRMS(ESI)calculated for C 32 H 33 INOS[M+H] + :606.1328, found:606.1328; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =20.80min(major),t R =30.24min(minor).

[0199] Example 29: Synthesis and Characterization of Compound 4ac

[0200] The same method as in Example 1 was used, wherein the substrate used was N-4-tert-butylbenzenecarbonylsulfenamide. Finally, the product 4ac was isolated with a yield of 98%, ee=91%, and dr=98:2.

[0201] The structure of compound 4ac is as follows:

[0202]

[0203] Characterization data of compound 4ac:

[0204] 4-(tert-butyl)-N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)benzamide(4ac): yield: 63.5 mg (98%), 98:2 dr; flash column chromatography eluent, petroleum ether / ethyl acetate = 5:1; white foam; [α] D 20 = -20.3 (c 0.51 CH2Cl2); 1 1H-NMR (600 MHz, CDCl3) δ 8.56 (d, J = 8.0 Hz, 1H), 8.17 (d, J = 8.2 Hz, 2H), 7.90 (d, J = 7.8 Hz, 1H), 7.60 (t, J = 7.8 Hz, 1H), 7.47 (d, J = 7.5 Hz, 1H), 7.38 (d, J = 8.0 Hz, 2H), 7.28 (d, J = 8.1 Hz, 2H), 7.19 (d, J = 8.3 Hz, 2H), 7.05 (t, J = 7.7 Hz, 1H), 7.00 (d, J = 7.5 Hz, 1H), 1.93 (s, 3H), 1.32 (s, 9H), 1.25 (s, 9H), 1.00 (s, 3H); 13 13C-NMR (151 MHz, CDCl3) δ 175.9, 155.7, 153.8, 143.1, 139.8, 139.8, 137.9, 137.6, 134.3, 133.9, 133.4, 132.9, 130.4, 130.1, 129.5, 129.4, 128.8, 126.3, 125.1, 124.7, 101.9, 35.1, 34.9, 31.4, 31.2, 19.9, 19.3; HRMS (ESI) calculated for C 35 H 39 INOS [M + H] +:648.1797, found: 648.1794; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =7.24min(major),t R =14.17min(minor).

[0205] Example 30: Synthesis and characterization of compound 4ad

[0206] The same method as in Example 1 was used, wherein the substrate used was N-4-methoxyphenylcarbonylsulfenamide. Finally, the product 4ad was isolated with a yield of 79%, ee=93%, and dr=98:2.

[0207] The structure of compound 4ad is as follows:

[0208]

[0209] Characterization data of compound 4ad:

[0210] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-4-methoxybenzamide(4ad):yield:49.0mg(79%),98:2dr; flash column chromatography eluent,petroleum ether / ethylacetate=5:1; white foam; [α] D 20 =10.2(c 0.13CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.52(d,J=7.9Hz,1H),8.19(d,J=7.6Hz,2H),7.89( d,J=7.7Hz,1H),7.60(t,J=7.8Hz,1H),7.47(d,J=7.4Hz,1H),7.28(d,J=8.0 Hz,2H),7.18(d,J=7.6Hz,2H),7.05(t,J=7.6Hz,1H),6.99(d,J=7.4Hz,1H) ,6.86(d,J=7.9Hz,2H),3.82(s,3H),1.93(s,3H),1.25(s,9H),0.99(s,3H); 13 C-NMR (151MHz, CDCl3) δ175.6,161.7,155.7,143.1,139.8,139.8,137.9,137.6,134.0,133.4,132.9,130.8,130 .4,130.0,129.8,129.5,129.4,126.3,125.0,113.0,101.9,55.4,35.1,31.2,19.9,19.3; HRMS(ESI)calculated for C 32 H 33 INO2S[M+H] + :622.1277, found: 622.1274; Enantiomeric excess: 93%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =33.32min(major),t R =66.62min(minor).

[0211] Example 31: Synthesis and characterization of compound 4ae

[0212] The same method as in Example 1 was used, wherein the substrate used was N-4-fluorophenylcarbonylsulfenamide. Finally, the product 4ae was isolated with a yield of 93%, ee=91%, and dr=98:2.

[0213] The structure of compound 4ae is as follows:

[0214]

[0215] Characterization data of compound 4ae:

[0216] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-4-fluorobenzamide(4ae):yield:56.6mg(93%),98:2dr;flash column chromatography eluent,petroleum ether / ethyl acetate=5:1;white foam;[α] D 20 =-12.3(c 0.10CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.50(d,J=8.0Hz,1H),8.26-8.20(m,2H),7.90(d,J=7.8Hz,1H),7.61(t,J=7.8Hz,1H),7.48(d,J=7.6Hz,1H),7.29(d,J=8.4Hz,2H),7.19(d,J=8.4Hz,2H),7.06(t,J=7.7Hz,1H),7.04-6.98(m,3H),1.93(s,3H),1.25(s,9H),0.99(s,3H); 13 C-NMR(151MHz,CDCl3)δ174.9,164.6(d,J=249.3Hz),155.9,143.1,139.8,139.7,138.0,137.6,133.5,131.2(d,J=8.7Hz),130.5,130.1,129.5,129.4,126.4,124.9,114.5(d,J=21.5Hz),101.9,35.1,31.2,19.9,19.3; 19 FNMR(564MHz,CDCl3)δ-106.38;HRMS(ESI)calculated for C 31 H 30 FINOS[M+H] + :610.1077,found:610.1073;Enantiomeric excess:91%,determined by HPLC(Daicel ChiralpakIC,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):t R=12.30min(major),t R =16.27min(minor).

[0217] Example 32: Synthesis and Characterization of Compound 4af

[0218] The same method as in Example 1 was used, wherein the substrate used was N-4-chlorophenylcarbonylsulfenamide. Finally, the product 4af was isolated with a yield of 85%, ee=91%, and dr=91:9.

[0219] The structure of compound 4af is as follows:

[0220]

[0221] Characterization data of compound 4af:

[0222] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-4-chlorobenzamide(4af):yield:53.1mg(85%),91:9dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 =15.2 (c 0.11 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.48(d,J=8.0Hz,1H),8.15(d,J=8.3Hz,2H),7.89(d,J=7.8Hz,1H),7.61(t,J=7.8Hz,1H),7.48(d,J=7.6Hz ,1H),7.31-7.28(m,4H),7.18(d,J=8.3Hz,2H),7.06(t,J=7.7Hz,1H),7.00(d,J=7.6Hz,1H),1.93(s,3H),1.25(s,9H),0.99(s,3H); 13C-NMR (151MHz, CDCl3) δ174.8,156.0,143.1,139.8,139.6,138.1,137.6,136.7,135.5,133.5,133.5,132 .4,130.5,130.1,129.5,129.4,127.9,126.4,124.8,101.8,35.1,31.1,19.9,19.3; HRMS(ESI)calculated forC 31 H 30 ClINOS[M+H] + :626.0781, found: 626.0783; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.22min(major),t R =12.71min(minor).

[0223] Example 33: Synthesis and characterization of compound 4ag

[0224] The same method as in Example 1 was used, wherein the substrate used was N-4-bromophenylcarbonylsulfenamide. Finally, the product 4ag was isolated with a yield of 96%, ee=90%, and dr=98:2.

[0225] The structure of compound 4ag is as follows:

[0226]

[0227] Characterization data of compound 4ag:

[0228] 4-bromo-N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphen yl]-2-yl)-λ 4 -sulfan-eylidene)benzamide(4ag):yield:64.4mg(96%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20=12.4 (c 0.21 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.47(d,J=8.0Hz,1H),8.09(d,J=8.4Hz,2H),7.89(d,J=7.8Hz,1H),7.61(t,J=7.8Hz,1H),7.50-7.45(m,3H ),7.29(d,J=8.4Hz,2H),7.18(d,J=8.4Hz,2H),7.06(t,J=7.7Hz,1H),7.00(d,J=7.6Hz,1H),1.93(s,3H),1.25(s,9H),1.00(s,3H); 13 C-NMR (151MHz, CDCl3) δ174.9,156.0,143.2,139.8,139.7,138.1,137.6,136.0,133.5,132.5,130.9,130 .7,130.5,130.1,129.5,129.4,126.4,125.3,124.9,101.8,35.1,31.2,19.9,19.3; HRMS(ESI)calculated forC 31 H 30 BrINOS[M+H] + :670.0276, found: 670.0279; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.73min(major),t R =14.17min(minor).

[0229] Example 34: Synthesis and Characterization of Compound 4ah

[0230] The same method as in Example 1 was used, wherein the substrate used was N-4-cyanobenzenecarbonylsulfenamide. Finally, the product 4ah was isolated with a yield of 94%, ee=89%, and dr=91:9.

[0231] The structure of compound 4ah is as follows:

[0232]

[0233] Characterization data of compound 4ah:

[0234] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-4-cyanobenzamide(4ah):yield:57.9mg(94%),91:9dr;flash column chromatography eluent,petroleum ether / ethyl acetate=5:1;white foam;[α] D 20 =13.2(c 0.19CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.46(d,J=7.9Hz,1H),8.30(d,J=7.8Hz,2H),7.90(d,J=7.7Hz,1H),7.68-7.59(m,3H),7.50(d,J=7.4Hz,1H),7.31(d,J=7.9Hz,2H),7.19(d,J=7.9Hz,2H),7.07(t,J=7.6Hz,1H),7.01(d,J=7.4Hz,1H),1.94(s,3H),1.25(s,9H),1.01(s,3H); 13 C-NMR(151MHz,CDCl3)δ173.8,156.2,143.2,141.2,139.8,139.5,138.3,137.6,133.7,133.1,132.1,131.7,130.6,130.1,129.5,129.5,129.5,126.5,124.8,119.1,113.8,101.8,35.2,31.2,19.9,19.3;HRMS(ESI)calculated for C 32 H 30 IN2OS[M+H] + :617.1124,found:617.1121;Enantiomeric excess:89%,determined by HPLC(Daicel Chiralpak IC,isopropanol / hexane=30 / 70,flowrate=1.0mL / min,T=30℃,λ=254nm):t R =25.55min(major),t R =32.19min(minor).

[0235] Example 35: Synthesis and characterization of compound 4ai

[0236] The same method as in Example 1 was used, wherein the substrate used was N-4-trifluoromethylphenylcarbonylsulfenamide. Finally, the product 4ai was isolated with a yield of 60%, ee=90%, and dr=96:4.

[0237] The structure of compound 4ai is as follows:

[0238]

[0239] Characterization data of compound 4ai:

[0240] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-4-(trifluoromethyl)benzamide(4ai):yield:39.5mg(60%),96:4dr; flash column chromatography eluent,petroleum ether / ethylacetate=5:1; white foam; [α] D 20 =8.8 (c 0.13CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.49(d,J=8.0Hz,1H),8.33(d,J=8.1Hz,2H),7.91(d,J=7.8Hz,1H),7.64-7.60(m,3H),7.50(d,J=7.6Hz,1H ),7.31(d,J=8.5Hz,2H),7.20(d,J=8.4Hz,2H),7.07(t,J=7.7Hz,1H),7.01(d,J=7.5Hz,1H),1.94(s,3H),1.26(s,9H),1.01(s,3H); 13 C-NMR (151MHz, CDCl3) δ174.4,156.1,143.2,139.8,139.7,138.2,137.6,133.7,132.2(q,J=33.2Hz),130.6,130 .1,129.5,129.5,129.3,126.5,124.9,124.8(q,J=3.6Hz),124.3(q,J=262.9Hz),101.8,35.2,31.2,19.9,19.3;19 F NMR(564MHz, CDCl3)δ-58.30; HRMS(ESI)calculated forC 32 H 30 F3INOS[M+H] + :660.1045, found: 660.1047; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =5.83min(major),t R =10.77min(minor).

[0241] Example 36: Synthesis and characterization of compound 4aj

[0242] The same method as in Example 1 was used, wherein the substrate used was N-3-fluorophenylcarbonylsulfenamide. Finally, the product 4aj was isolated with a yield of 98%, ee=90%, and dr=95:5.

[0243] The structure of compound 4aj is as follows:

[0244]

[0245] Characterization data of compound 4aj:

[0246] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-fluorobenzamide(4aj):yield:59.7mg(98%),95:5dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 = -6.7 (c 0.27 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.51(d,J=8.0Hz,1H),8.00(d,J=7.7Hz,1H),7.93(d,J=10.0Hz,1H),7.90(d,J=7.8Hz,1H),7.62(t,J=7.8Hz,1H),7.4 9(d,J=7.6Hz,1H),7.34-7.27(m,3H),7.19(d,J=8.1Hz,2H),7.11-7.0 3(m,2H),7.00(d,J=7.5Hz,1H),1.93(s,3H),1.25(s,9H),1.00(s,3H); 13 C-NMR (151MHz, CDCl3) δ174.5 (d, J = 2.5Hz), 162.5 (d, J = 244.7Hz), 156.0, 14 3.1,139.8,139.6,139.4(d,J=6.8Hz),138.0,137.5,133.6,133.3,132.3,13 0.5,130.1,129.5,129.5,129.2(d,J=7.7Hz),126.4,124.8,124.6(d,J=2.7H z),117.4(d,J=21.4Hz),115.8(d,J=22.3Hz),101.8,35.1,31.1,19.8,19.3; 19 F NMR (471MHz, CDCl3) δ-114.22; HRMS (ESI) calculated for C 31 H 30 FINOS[M+H] + :610.1077, found:610.1078; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =5.89min(major),t R =8.11min(minor).

[0247] Example 37: Synthesis and Characterization of Compound 4ak

[0248] The same method as in Example 1 was used, wherein the substrate used was N-3-chlorobenzenecarbonylsulfenamide. Finally, the product 4ak was isolated with a yield of 84%, ee=92%, and dr=98:2.

[0249] The structure of compound 4ak is as follows:

[0250]

[0251] Characterization data of compound 4ak:

[0252] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-chlorobenzamide(4ak):yield:52.5mg(84%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 = -7.8 (c 0.22CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.50(d,J=8.0Hz,1H),8.23(s,1H),8.08(d,J=7.6Hz,1H),7.90(d,J=7.8Hz,1H),7.62(t,J=7.8Hz,1H),7.49(d,J=7.5Hz,1H) ,7.37(d,J=7.9Hz,1H),7.34-7.27(m,3H),7.19(d,J=8.3Hz,2H),7.06(t,J =7.7Hz,1H),7.00(d,J=7.5Hz,1H),1.94(s,3H),1.26(s,9H),1.00(s,3H); 13 C-NMR (151MHz, CDCl3) δ174.4,156.0,143.2,139.8,139.7,138.9,138.1,137.6,133.8,133.6,133.4,132.4,130.6, 130.5,130.1,129.5,129.5,129.2,129.1,127.1,126.4,124.9,101.9,35.2,31.2,19.9,19.3; HRMS(ESI)calculated for C 31 H 30 ClINOS[M+H] +:626.0781, found: 626.0780; Enantiomeric excess: 92%, determined by HPLC (Daicel ChiralpakIC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =10.04min(major),t R =17.70min(minor).

[0253] Example 38: Synthesis and Characterization of Compound 4al

[0254] The same method as in Example 1 was used, wherein the substrate used was N-3-bromophenylcarbonylsulfenamide. Finally, the product 4a1 was isolated with a yield of 86%, ee=87%, and dr=98:2.

[0255] The structure of compound 4al is as follows:

[0256]

[0257] Characterization data of compound 4al:

[0258] 3-bromo-N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphen yl]-2-yl)-λ 4 -sulfan-eylidene)benzamide(4al):yield:58.4mg(87%),92:8dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20 = -9.8 (c 0.18 CH2Cl2); 1H-NMR (600MHz, CDCl3) δ8.49(d,J=8.0Hz,1H),8.39(s,1H),8.13(d,J=7.7Hz,1H),7.90(d,J=7.9Hz,1H),7.63(t,J=7.8Hz,1H),7.52(d,J=7.8Hz,1H) ,7.49(d,J=7.4Hz,1H),7.30(d,J=8.1Hz,2H),7.24-7.16(m,3H),7.06(t,J =7.6Hz,1H),7.00(d,J=7.4Hz,1H),1.94(s,3H),1.26(s,9H),1.00(s,3H); 13 C-NMR (101MHz, CDCl3) δ174.3,156.0,143.1,139.8,139.6,139.0,138.1,137.5,133.6,133.5,133.3,132.2,132.1, 130.5,130.1,129.5,129.5,129.4,127.5,126.4,124.8,122.0,101.8,35.1,31.2,19.8,19.3; HRMS(ESI)calculated for C 31 H 30 BrINOS[M+H] + :670.0276, found: 670.0279; Enantiomeric excess: 93%, determined by HPLC (Daicel ChiralpakIC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =10.25min(major),t R =20.34min(minor).

[0259] Example 39: Synthesis and characterization of compound 4am

[0260] The same method as in Example 1 was used, wherein the substrate used was N-3-methoxyphenylcarbonylsulfenamide. Finally, the product 4am was isolated with a yield of 87%, ee=91%, and dr=86:14.

[0261] The structure of compound 4am is as follows:

[0262]

[0263] Characterization data of compound 4am:

[0264] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-methoxybenzamide(4am):yield:54.0mg(87%),86:14dr;flash column chromatography eluent,petroleum ether / ethylacetate=3:1;white foam;[α] D 20 =-10.3(c 0.24CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.53(d,J=7.9Hz,1H),7.90(d,J=8.2Hz,1H),7.88(d,J=7.7Hz,1H),7.76(s,1H),7.61(t,J=7.2Hz,1H),7.48(d,J=7.3Hz,1H),7.31-7.25(m,3H),7.19(d,J=7.3Hz,2H),7.06(t,J=7.6Hz,1H),7.00(d,J=7.4Hz,1H),6.97(d,J=7.9Hz,1H),3.83(s,3H),1.93(s,3H),1.25(s,9H),0.99(s,3H); 13 C-NMR(101MHz,CDCl3)δ175.7,159.3,155.8,143.1,139.8,139.7,138.5,137.9,137.5,133.6,133.4,132.6,130.4,130.1,129.5,129.4,128.7,126.3,124.9,121.6,117.2,113.4,101.9,55.5,35.1,31.2,19.8,19.3;HRMS(ESI)calculatedfor C 32 H 33 INO2S[M+H] + :622.1277,found:622.1273;Enantiomeric excess:91%,determined by HPLC(Daicel Chiralpak IF,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):tR =8.95min(major),t R =15.18min(minor).

[0265] Example 40: Synthesis and characterization of compound 4an

[0266] The same method as in Example 1 was used, wherein the substrate used was N-3,5-dichlorobenzenecarbonylsulfenamide. Finally, the product 4an was isolated with a yield of 85%, ee=92%, and dr=94:6.

[0267] The structure of compound 4an is as follows:

[0268]

[0269] Characterization data of compound 4an:

[0270] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3,5-dichlorobenzamide(4an):yield:56.0mg(85%),94:6dr; flash column chromatography eluent,petroleum ether / ethylacetate=5:1; white foam; [α] D 20 = -18.5 (c 0.12CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.45(d,J=8.0Hz,1H),8.09(s,2H),7.90(d,J=7.7Hz,1H),7.63(t,J=7.7Hz,1H),7.50(d,J=7.5Hz,1H),7.38(s ,1H),7.31(d,J=8.0Hz,2H),7.19(d,J=8.0Hz,2H),7.06(t,J=7.6Hz,1H),7.01(d,J=7.5Hz,1H),1.94(s,3H),1.26(s,9H),1.00(s,3H); 13C-NMR (151MHz, CDCl3) δ173.0,156.2,143.2,140.1,139.8,139.6,138.2,137.6,134.4,133.7,133.1,132.1, 130.6,130.3,130.1,129.6,129.5,127.5,126.5,124.8,101.8,35.2,31.2,19.9,19.3; HRMS(ESI)calculated for C 31 H 29 Cl2INOS[M+H] + :660.0392, found: 660.0387; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =10.92min(major),t R =15.22min(minor).

[0271] Example 41: Synthesis and characterization of compound 4ao

[0272] The same method as in Example 1 was used, wherein the substrate used was N-2-naphthylcarbonylsulfenamide. Finally, the product 4ao was isolated with a yield of 94%, ee=91%, and dr=97:3.

[0273] The structure of compound 4ao is as follows:

[0274]

[0275] Characterization data of compound 4ao:

[0276] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-2-naphthamide(4ao):yield:60.3mg(94%),97:3dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; white foam; [α] D 20=8.0 (c 0.17CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.76(s,1H),8.57(d,J=7.9Hz,1H),8.34(d,J=8.4Hz,1H),7.91(t,J=9.0Hz,2H),7.81(t,J=7.5Hz,2H),7.62(t,J=7.6Hz,1H) ,7.50-7.41(m,3H),7.29(d,J=7.7Hz,2H),7.23(d,J=7.8Hz,2H),7.05(t,J =7.5Hz,1H),6.99(d,J=7.3Hz,1H),1.93(s,3H),1.25(s,9H),1.00(s,3H); 13 C-NMR (151MHz, CDCl3) δ175.9,155.8,143.2,139.8,138.0,137.6,134.8,134.4,133.8,133.5,133.0,132.6,130.4,130.1,129 .6,129.4,129.3,129.2,127.7,127.2,126.8,126.4,126.3,125.9,125.0,101.9,35.1,31.2,19.9,19.3; HRMS(ESI)calculated for C 35 H 33 INOS[M+H] + :642.1328, found: 642.1325; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =10.15min(major),t R =16.69min(minor).

[0277] Example 42: Synthesis and Characterization of Compound 4ap

[0278] The same method as in Example 1 was used, wherein the substrate used was N-2-furanylcarbonylsulfenamide. Finally, the product 4ap was isolated with a yield of 81%, ee=89%, and dr=98:2.

[0279] The structure of compound 4ap is as follows:

[0280]

[0281] Characterization data of compound 4ap:

[0282] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)furan-2-carboxamide(4ap): yield: 47.1 mg (81%), 98:2 dr; flash column chromatography eluent, petroleum ether / ethyl acetate = 5:1; white foam; [α] D 20 = -10.2 (c 0.47 CH2Cl2); 1 1H-NMR (600 MHz, CDCl3) δ 8.45 (d, J = 7.7 Hz, 1H), 7.90 (d, J = 7.4 Hz, 1H), 7.60 (t, J = 7.3 Hz, 1H), 7.50 - 7.43 (m, 2H), 7.29 (d, J = 7.4 Hz, 2H), 7.19 (d, J = 7.7 Hz, 2H), 7.08 - 7.02 (m, 2H), 6.98 (d, J = 6.7 Hz, 1H), 6.40 (s, 1H), 1.93 (s, 3H), 1.25 (s, 9H), 0.98 (s, 3H); 13 13C-NMR (151 MHz, CDCl3) δ 168.1, 156.0, 151.4, 143.9, 143.0, 139.7, 139.6, 138.0, 137.6, 133.5, 133.4, 132.0, 130.4, 130.0, 129.7, 129.4, 126.4, 124.8, 113.8, 111.2, 101.8, 35.1, 31.1, 19.8, 19.2; HRMS(ESI) calculated for C 29 H 29 INO2S [M + H] + : 582.0964, found: 582.0967; Enantiomeric excess: 89%, determined by HPLC (Daicel Chiralpak IA, isopropanol / hexane = 5 / 95, flow rate = 1.0 mL / min, T = 30 °C, λ = 254 nm): t R = 28.95 min (major), tR =62.80min(minor).

[0283] Example 43: Synthesis and Characterization of Compound 4aq

[0284] The same method as in Example 1 was used, wherein the substrate used was N-2-thienylcarbonylsulfenamide. Finally, the product 4aq was isolated with a yield of 85%, ee=92%, and dr=98:2.

[0285] The structure of compound 4aq is as follows:

[0286]

[0287] Characterization data of compound 4aq:

[0288] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)thiophene-2-carboxamide(4aq):yield:50.7mg(85%),98:2dr; flash column chromatography eluent,petroleum ether / ethylacetate=5:1; white foam; [α] D 20 = -18.2 (c 0.21 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.52(d,J=7.8Hz,1H),7.90(d,J=7.9Hz,1H),7.73(s,1H),7.61(t,J=7.7Hz,1H),7.47(d,J=7.4Hz,1H),7.34( s,1H),7.28(d,J=7.5Hz,2H),7.17(d,J=8.0Hz,2H),7.05(t,J=7.6Hz,1H),7.02-6.96(m,2H),1.93(s,3H),1.25(s,9H),0.98(s,3H); 13C-NMR (101MHz, CDCl3) δ171.2,155.9,143.0,142.2,139.8,139.6,138.0,137.6,133.5,132.4,130.5,130 .1,129.9,129.5,129.5,129.1,127.2,126.4,124.9,101.9,35.1,31.2,19.8,19.3; HRMS(ESI)calculated for C 29 H 29 F3INOS2[M+H] + :598.0735, found: 598.0735; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =8.40min(major),t R =13.24min(minor).

[0289] Example 44: Synthesis and Characterization of Compound 4ar

[0290] The same method as in Example 1 was used, wherein the substrate used was N-4-bromo-2-thienylcarbonylsulfenamide. Finally, the product 4ar was isolated with a yield of 83%, ee=90%, and dr=98:2.

[0291] The structure of compound 4ar is as follows:

[0292]

[0293] Characterization data of compound 4ar:

[0294] 4-bromo-N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphen yl]-2-yl)-λ 4 -sulfan-eylidene)thiophene-2-carboxamide(4ar):yield:56.2mg(83%),98:2dr; flash column chromatography eluent,petroleum ether / ethylacetate=5:1; white foam; [α] D 20=7.3 (c 0.16CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.46(d,J=7.6Hz,1H),7.90(d,J=6.9Hz,1H),7.67-7.55(m,2H),7.49(d,J=6.5Hz,1H),7.29(d,J=7.4H z,2H),7.22(s,1H),7.16(d,J=7.5Hz,2H),7.06(t,J=7.0Hz,1H),6.99(d,J=6.3Hz,1H),1.93(s,3H),1.25(s,9H),0.98(s,3H); 13 C-NMR (151MHz, CDCl3) δ169.7,156.2,143.4,143.1,139.8,139.6,138.1,137.6,133.7,133.3,132.2,132.0, 130.5,130.1,129.5,129.5,126.5,126.4,124.8,109.6,101.8,35.2,31.2,19.9,19.3; HRMS(ESI)calculated for C 29 H 28 BrINOS2[M+H] + :675.9840, found: 675.9843; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flowrate=1.0mL / min, T=30℃, λ=254nm): t R =21.14min(major),t R =32.27min(minor).

[0295] Example 45: Synthesis and characterization of compound 4as

[0296] The same method as in Example 1 was used, wherein the substrate used was N-cyclopropylcarbonylsulfenamide. Finally, the product 4as was isolated with a yield of 99%, ee=92%, and dr=98:2.

[0297] The structure of compound 4as is as follows:

[0298]

[0299] Characterization data of compound 4as:

[0300] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)cyclopropanecarboxamide(4as):yield:54.9mg(99%),98:2dr;flash column chromatography eluent,petroleum ether / ethylacetate=5:1;white foam;[α] D 20 =-39.2(c 0.21CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.32(d,J=8.0Hz,1H),7.87(d,J=7.8Hz,1H),7.58(t,J=7.8Hz,1H),7.45(d,J=7.6Hz,1H),7.28(d,J=8.1Hz,2H),7.12(d,J=8.2Hz,2H),7.02(t,J=7.7Hz,1H),6.95(d,J=7.5Hz,1H),1.95-1.88(m,4H),1.26(s,9H),0.96(s,3H),0.94-0.86(m,2H),0.72-0.67(m,1H),0.67-0.61(m,1H); 13 C-NMR(151MHz,CDCl3)δ183.9,155.7,142.9,139.7,139.6,137.9,137.4,133.7,133.3,132.2,130.3,129.9,129.5,129.3,126.4,124.4,101.8,35.1,31.1,19.8,19.2,16.4,7.9,7.7;HRMS(ESI)calculated for C 28 H 31 INOS[M+H] + :556.1171,found:556.1172;Enantiomeric excess:92%,determined by HPLC(Daicel Chiralpak IF,isopropanol / hexane=20 / 80,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =8.14min(major),t R=10.45min(minor).

[0301] Example 46: Synthesis and characterization of compound 4at

[0302] The same method as in Example 1 was used, wherein the substrate used was N-cyclohexylcarbonylsulfenamide. Finally, the product 4at was isolated with a yield of 73%, ee=92%, and dr=98:2.

[0303] The structure of compound 4at is as follows:

[0304]

[0305] Characterization data of compound 4at:

[0306] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e) cyclohexanecarboxamide (4at): yield: 43.6mg (73%), 98:2dr; flash column chromatography eluent, petroleum ether / ethylacetate=5:1; white foam; [α] D 20 = -25.2 (c 0.14CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.25(d,J=7.9Hz,1H),7.87(d,J=7.6Hz,1H),7.56(t,J=7.8Hz ,1H),7.44(d,J=7.0Hz,1H),7.27(d,J=8.7Hz,2H),7.10(d,J=7.2Hz,2H),7.02(t,J=7 .4Hz,1H),6.97(d,J=7.2Hz,1H),2.50-2.44(m,1H),2.00(d,J=13.8Hz,1H),1.91(s,3 H),1.77-1.71(m,2H),1.69-1.61(m,3H),1.25(s,9H),0.98(s,3H),0.90-0.83(m,4H); 13C-NMR (151MHz, CDCl3) δ187.0,155.6,143.2,139.9,139.6,137.9,137.5,133.9,133.2,132.4,130.3,129.9,129 .4,129.3,126.3,124.5,101.9,46.5,35.1,31.2,30.8,30.5,26.3,26.2,26.2,19.9,19.3; HRMS(ESI)calculated for C 31 H 37 INOS[M+H] + :598.1641, found: 598.1639; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =8.12min(major),t R =9.95min(minor).

[0307] Example 47: Synthesis and Characterization of Compound 4au

[0308] The same method as in Example 1 was used, wherein the substrate used was N-n-propylcarbonylsulfenamide. Finally, the product 4au was isolated with a yield of 99%, ee=92%, and dr=98:2.

[0309] The structure of compound 4au is as follows:

[0310]

[0311] Characterization data of compound 4au:

[0312] N-((S,E)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)butyramide(4au):yield:55.1mg(99%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=5:1; colorless oil; [α] D 20= -29.5 (c 0.55 CH3OH); 1 H-NMR (600MHz, CDCl3) δ8.27(d,J=7.6Hz,1H),7.87(d,J=7.4Hz,1H),7.57(t ,J=7.5Hz,1H),7.45(d,J=7.1Hz,1H),7.28(d,J=7.9Hz,2H),7.13(d,J=7.7H z,2H),7.02(t,J=7.3Hz,1H),6.98(d,J=7.0Hz,1H),2.44-2.35(m,2H),1.92 (s,3H),1.74-1.66(m,2H),1.25(s,9H),1.00(s,3H),0.93(t,J=7.0Hz,3H); 13 C-NMR (151MHz, CDCl3) δ184.1,155.6,143.1,139.8,139.5,137.9,137.5,133.7,133.3,132.3,130.3,12 9.9,129.4,129.3,126.3,124.7,101.8,40.0,35.1,31.1,20.2,19.9,19.3,14.2; HRMS(ESI)calculated for C 28 H 33 INOS[M+H] + :558.1328, found:558.1323; Enantiomeric excess:92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =14.84min(major),t R =22.81min(minor).

[0315] Example 48: Synthesis and Characterization of Compound 4av

[0316] The same method as in Example 1 was used, wherein the substrate used was N-isopropylcarbonylsulfenamide. Finally, the product 4av was isolated with a yield of 99%, ee=91%, and dr>98:2.

[0317] The structure of compound 4av is as follows:

[0318]

[0319] Characterization data of compound 4av:

[0320] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e)isobutyramide(4av):yield:55.1mg(99%),>98:2dr;flash column chromatography eluent,petroleum ether / ethyl acetate=5:1;colorless oil;[α] D 20 =-30.5(c 0.56CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.27(d,J=8.0Hz,1H),7.87(d,J=7.8Hz,1H),7.56(t,J=7.8Hz,1H),7.44(d,J=7.6Hz,1H),7.28(d,J=7.7Hz,2H),7.11(d,J=8.0Hz,2H),7.03(t,J=7.7Hz,1H),6.97(d,J=7.5Hz,1H),2.78-2.72(m,1H),1.91(s,3H),1.26(s,9H),1.21(d,J=6.9Hz,3H),1.14(d,J=6.9Hz,3H),0.99(s,3H); 13 C-NMR(151MHz,CDCl3)δ187.8,155.6,143.2,139.8,139.6,137.9,137.5,133.8,133.2,132.4,130.3,129.9,129.3,129.3,126.3,124.6,101.8,36.5,35.1,31.2,20.7,20.5,19.9,19.2;HRMS(ESI)calculated for C 28 H 33 INOS[M+H] + :558.1328,found:558.1325;Enantiomeric excess:91%,determined by HPLC(Daicel Chiralpak IF,isopropanol / hexane=10 / 90,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =10.85min(major),tR =16.99min(minor).

[0321] Example 49: Synthesis and Characterization of Compound 4aw

[0322] The same method as in Example 1 was used, wherein the substrate used was N-tert-butylcarbonylsulfenamide. Finally, the product 4aw was isolated with a yield of 96%, ee=93%, and dr=98:2.

[0323] The structure of compound 4aw is as follows:

[0324]

[0325] Characterization data of compound 4aw:

[0326] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneyliden-e) pivalamide (4aw): yield: 54.8mg (96%), 98:2dr; flash column chromatography eluent, petroleum ether / ethyl acetate=5:1; colorless oil; [α] D 20 = -13.9 (c 0.55 CH3OH); 1 H-NMR (600MHz, CDCl3) δ8.40(d,J=8.0Hz,1H),7.86(d,J=7.7Hz,1H),7.57(t,J=7.8Hz,1H),7.43(d,J=7.5Hz,1H),7.25(d,J=8.1 Hz,2H),7.07(d,J=8.0Hz,2H),7.03(t,J=7.7Hz,1H),6.98(d,J=7.5Hz,1H),1.90(s,3H),1.25(s,9H),1.24(s,9H),0.97(s,3H); 13C-NMR (151MHz, CDCl3) δ189.4,155.3,143.2,140.0,139.7,137.7,137.5,134.3,133.4,133.1,130.3 ,130.0,129.2,129.1,126.2,125.1,102.0,40.3,35.1,31.2,28.9,19.9,19.3; HRMS(ESI)calculated for C 29 H 35 INOS[M+H] + :572.1484, found: 572.1480; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =5.41min(major),t R =7.35min(minor).

[0327] Example 50: Synthesis and characterization of compound 4ax

[0328] The same method as in Example 1 was used, wherein the substrate used was N-3-indolylmethylenecarbonylsulfenamide. Finally, the product 4ax was isolated with a yield of 56%, ee=82%, and dr=94:6.

[0329] The structure of compound 4ax is as follows:

[0330]

[0331] Characterization data of compound 4ax:

[0332] N-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-2-(1H-indol-3-yl)acetamide(4ax):yield:36.1mg(56%),94:6dr; flash column chromatography eluent, petroleum ether / ethylacetate=3:1; slight yellow foam; [α] D 20= -12.2 (c 0.16CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.46 (s, 1H), 8.18 (d, J = 5.8Hz, 1H), 7.85 (d, J = 7.9Hz, 1H),7.75(d,J=7.4Hz,1H),7.44-7.38(m,2H),7.23(d,J=7.9Hz,2H),7.20(d, J=7.7Hz,1H),7.12-6.99(m,5H),6.96(d,J=7.5Hz,1H),6.84(s,1H),3.91(d, J=15.1Hz,1H),3.82(d,J=15.1Hz,1H),1.89(s,3H),1.23(s,9H),0.98(s,3H); 13 C-NMR (101MHz, CDCl3) δ182.5,155.8,143.1,139.8,139.5,137.9,137.5,136.4,133.5,133.3,132.3,131.8,130.3,129.9,129.6, 129.3,127.9,126.3,124.8,123.5,121.3,119.6,118.7,111.3,111.2,101.8,35.1,34.7,31.2,19.9,19.3; HRMS(ESI)calculated for C 34 H 34 IN2OS[M+H] + :645.1437, found: 645.1438; Enantiomeric excess: 82%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =42.82min(major),t R =37.31min(minor).

[0333] Example 51: Synthesis and characterization of compound 4ay

[0334] The same method as in Example 1 was used, wherein the substrate used was N-anilinocarbonylsulfenamide. Finally, the product 4ay was isolated with a yield of 99%, ee=92%, and dr>98:2.

[0335] The structure of compound 4ay is as follows:

[0336]

[0337] Characterization data of compound 4ay:

[0338] 1-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-phenylurea(4ay): yield: 60.0 mg (99%), >98:2 dr; flash column chromatography eluent, petroleum ether / ethyl acetate = 3:1; white foam; [α] D 20 = 13.4 (c 0.69 CH2Cl2); 1 1H-NMR (600 MHz, CDCl3) δ 8.32 (d, J = 7.9 Hz, 1H), 7.89 (d, J = 7.7 Hz, 1H), 7.58 (t, J = 7.8 Hz, 1H), 7.45 (d, J = 7.6 Hz, 1H), 7.42 (d, J = 7.8 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H), 7.23 - 7.11 (m, 4H), 7.08 - 7.01 (m, 2H), 6.97 (d, J = 7.5 Hz, 1H), 6.88 (t, J = 7.3 Hz, 1H), 1.93 (s, 3H), 1.26 (s, 9H), 1.04 (s, 3H); 13 13C-NMR (101 MHz, CDCl3) δ 163.3, 155.8, 142.6, 140.7, 139.7, 139.5, 137.9, 137.5, 135.1, 133.3, 133.2, 130.4, 130.0, 129.3, 129.0, 128.7, 126.5, 124.2, 121.3, 118.1, 101.9, 35.1, 31.2, 20.0, 19.3; HRMS (ESI) calculated for C 31 H 32 IN2OS [M + H] + : 607.1280, found: 607.1273; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane = 30 / 70, flow rate = 1.0 mL / min, T = 30 °C, λ = 254 nm): tR =9.91min(major),t R =15.28min(minor).

[0339] Example 52: Synthesis and Characterization of Compound 4az

[0340] The same method as in Example 1 was used, wherein the substrate used was N-4-methylanilinocarbonylsulfenamide. Finally, the product 4az was isolated with a yield of 97%, ee=92%, and dr=98:2.

[0341] The structure of compound 4az is as follows:

[0342]

[0343] Characterization data of compound 4az:

[0344] 1-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-(p-tolyl)urea(4az):yield:60.1mg(97%),98:2dr; flash column chromatography eluent,petroleum ether / ethyl acetate=3:1; white foam; [α] D 20 =10.8 (c 0.13CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.30(d,J=8.3Hz,1H),7.89(d,J=7.0Hz,1H),7.58(t,J=7.3Hz,1H),7.46(d,J=7.6Hz,1H),7.31(t,J=8.4Hz,4H ),7.26(s,1H),7.15(d,J=8.1Hz,2H),7.01(t,J=8.9Hz,3H),6.97(d,J=7.0Hz,1H),2.24(s,3H),1.93(s,3H),1.26(s,9H),1.04(s,3H); 13C-NMR (101MHz, CDCl3) δ155.8,142.6,139.8,139.5,138.2,138.0,137.6,133.3,130.8,130.4,130.0, 129.4,129.3,129.1,126.5,124.2,118.3,101.9,35.2,31.2,20.8,20.0,19.3; HRMS(ESI)calculated forC 32 H 34 IN2OS[M+H] + :621.1437, found: 621.1437; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =11.41min(major),t R =18.35min(minor).

[0345] Example 53: Synthesis and characterization of compound 4ba

[0346] The same method as in Example 1 was used, wherein the substrate used was N-4-chloroanilinocarbonylsulfenamide. Finally, the product 4ba was isolated with a yield of 99%, ee=92%, and dr=95:5.

[0347] The structure of compound 4ba is as follows:

[0348]

[0349] Characterization data of compound 4ba:

[0350] 1-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-(4-chlorophenyl)urea(4ba):yield:63.4mg(99%),95:5dr; flash column chromatography eluent,petroleum ether / ethylacetate=3:1; white foam; [α] D 20= -31.6 (c 0.65 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.04(d,J=8.0Hz,1H),7.60(d,J=7.8Hz,1H),7.55(t,J=7.7Hz,1H),7.47-7.44(m,1H),7.37(d,J=8.7Hz,3H),7.33 (d,J=7.1Hz,2H),7.22(d,J=6.9Hz,2H),7.13(d,J=6.9Hz,2H),7.08(s,1H),7.04(t,J=6.0Hz,1H),2.34(s,3H),2.01(s,3H),1.28(s,9H); 13 C-NMR (101MHz, CDCl3) δ163.2,156.3,142.7,139.7,139.6,139.3,138.3,136.9,135.0,133.6,130.8,130.6, 130.5,129.5,129.4,128.7,127.0,126.2,123.3,119.2,103.1,35.2,31.2,22.3,19.6; HRMS(ESI)calculated for C 31 H 31 ClIN2OS[M+H] + :641.0890, found: 641.0887; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =8.72min(major),t R =14.19min(minor).

[0351] Example 54: Synthesis and Characterization of Compound 4bb

[0352] The same method as in Example 1 was used, wherein the substrate used was N-4-bromoanilinocarbonylsulfenamide. Finally, the product 4bb was isolated with a yield of 99%, ee=92%, and dr=97:3.

[0353] The structure of compound 4bb is as follows:

[0354]

[0355] Characterization data of compound 4bb:

[0356] 1-(4-bromophenyl)-3-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)urea(4bb):yield:67.9mg(99%),97:3dr;flash column chromatography eluent,petroleum ether / ethylacetate=3:1;white foam;[α] D 20 =30.1(c 0.43CH2Cl2); 1 H-NMR(600MHz,CDCl3)δ8.29(d,J=7.6Hz,1H),7.89(d,J=7.7Hz,1H),7.58(t,J=7.9Hz,1H),7.46(d,J=7.4Hz,1H),7.31-7.23(m,6H),7.15(d,J=7.6Hz,2H),7.09(s,1H),7.04(t,J=6.8Hz,1H),6.98(d,J=7.1Hz,1H),1.93(s,3H),1.26(s,9H),1.04(s,3H); 13 C-NMR(101MHz,CDCl3)δ163.1,156.0,142.6,139.9,139.6,139.5,138.1,137.6,134.9,133.4,133.0,131.5,130.4,130.0,129.4,129.0,126.6,124.1,119.7,113.5,101.9,35.2,31.2,20.0,19.3;HRMS(ESI)calculated for C 31 H 31 BrIN2OS[M+H] + :685.0385,found:685.0383;Enantiomeric excess:92%,determined by HPLC(Daicel Chiralpak IF,isopropanol / hexane=30 / 70,flowrate=1.0mL / min,T=30℃,λ=254nm):t R =9.48min(major),t R =15.47min(minor).

[0357] Example 55: Synthesis and Characterization of Compound 4bc

[0358] The same method as in Example 1 was used, wherein the substrate used was N-4-methylformate anilinocarbonylsulfenamide. Finally, the product 4bc was isolated with a yield of 79%, ee=92%, and dr=98:2.

[0359] The structure of compound 4bc is as follows:

[0360]

[0361] Characterization data of compound 4bc:

[0362] Methyl-4-(3-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphen yl]-2-yl)-λ 4 -sulfaneylidene)ureido)benzoate(4bc):yield:52.5mg(79%),98:2dr; flash column chromatography eluent, petroleum ether / ethylacetate=1:1; white foam; [α] D 20 =13.5 (c 0.32 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.29(d,J=8.1Hz,1H),7.92-7.85(m,3H),7.59(t,J=7.2Hz,1H),7.47(d,J=8.3Hz,3H),7.31(d,J=8.2Hz,2H), 7.24(s,1H),7.16(d,J=8.2Hz,2H),7.04(t,J=7.3Hz,1H),6.98(d,J=7.6Hz,1H),3.85(s,3H),1.94(s,3H),1.26(s,9H),1.05(s,3H); 13C-NMR (101MHz, CDCl3) δ167.2,162.9,156.1,145.2,142.7,139.6,139.5,138.1,137.6,134.7,133.5,132.8,130.8, 130.5,130.1,129.4,129.1,126.6,124.2,122.6,117.0,101.9,51.8,35.2,31.2,20.0,19.3; HRMS(ESI)calculated for C 33 H 34 IN2O3S[M+H] + :665.1335, found: 665.1345; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30℃, λ=254nm): t R =16.49min(major),t R =27.51min(minor).

[0363] Example 56: Synthesis and Characterization of Compound 4bd

[0364] The same method as in Example 1 was used, wherein the substrate used was N-4-methoxyanilinocarbonylsulfenamide. Finally, the product 4bd was isolated with a yield of 99%, ee=93%, and dr>98:2.

[0365] The structure of compound 4bd is as follows:

[0366]

[0367] Characterization data of compound 4bd:

[0368] 1-((S)-(4-(tert-butyl)phenyl)((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)-λ 4 -sulfaneylidene)-3-(4-methoxyphenyl)urea(4bd):yield:63.0mg(99%),>98:2dr; flash column chromatography eluent, petroleum ether / ethylacetate=2:1; white foam; [α] D20 =7.2 (c 0.19 CH2Cl2); 1 H-NMR (600MHz, CDCl3) δ8.30(d,J=7.6Hz,1H),7.89(d,J=7.3Hz,1H),7.58(t,J =6.8Hz,1H),7.45(d,J=7.3Hz,1H),7.34(d,J=7.2Hz,2H),7.30(d,J=7.8Hz,2H ),7.26(s,1H),7.15(d,J=7.9Hz,2H),7.03(t,J=7.1Hz,1H),6.97(d,J=8.0Hz, 1H),6.77(d,J=8.0Hz,2H),3.74(s,3H),1.93(s,3H),1.26(s,9H),1.04(s,3H); 13 C-NMR (101MHz, CDCl3) δ154.6,142.6,139.8,139.5,137.6,130.0,129.1,126.5, 125.1,120.0,114.1,101.9,55.7,35.2,31.2,20.0,19.3; HRMS(ESI)calculated for C 32 H 34 IN2O2S[M+H] + :637.1386, found: 637.1383; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=30 / 70, flowrate=1.0mL / min, T=30℃, λ=254nm): t R =16.36min(major),t R =26.03min(minor).

[0369] Table 1 Synthesis of axial chiral sulfilimines in the present invention

[0370]

[0371]

[0372] The preferred embodiments of the present invention are described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

[0373] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention will not further describe various possible combinations.

[0374] In addition, various embodiments of the present invention may be arbitrarily combined, and as long as they do not violate the concept of the present invention, they should also be regarded as the contents disclosed by the present invention.

Claims

1. An axially chiral sulfilimine compound, characterized in that: The general structural formula of the axially chiral sulfilimine compound is: Among them, R 1 C 1-6 Straight chain or branched alkyl / cycloalkyl, C 6-10 One of aryl or substituted aryl, naphthyl, furyl, thienyl, indolyl and anilino; The substituted aryl group is C 1-6 Alkyl substituted aryl, C 1-3 One of an aryl group substituted with an oxyalkyl group, an aryl group substituted with a nitro group, an aryl group substituted with a trifluoromethyl group, an aryl group substituted with a cyano group, or a halogenated aryl group; R 2 C 4-7 Straight or branched alkyl, cyclohexyl, C 6-10 One of aryl or substituted aryl, naphthyl, thienyl, and substituted benzyl; R 3 and R 4 Each of them is one of hydrogen, alkyl and halogen; R 5 and R 6 Each of them is one of hydrogen, alkyl and trifluoromethyl.

2. The axially chiral sulfilimine compound according to claim 1, wherein The alkyl group is one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl and isooctyl.

3. The axially chiral sulfilimine compound according to claim 1, wherein The cycloalkyl group is one of cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

4. The axially chiral sulfilimine compound according to claim 1, wherein The halogen is one of fluorine, chlorine, bromine or iodine.

5. The method for preparing the axially chiral sulfilimine compound according to any one of claims 1 to 4, characterized in that: The preparation method comprises: The sulfenamide, cyclic diaryliodonium salt, tetraethylcyanocopper hexafluorophosphate, metal-centered chiral cobalt (III) complex anion and lithium acetate are mixed under the protection of an inert gas, and then dichloromethane is added, and the reaction is carried out at -12°C to -8°C for 34 to 38 hours, and the axial chiral sulfilimine compound is separated and purified; 6. The preparation method according to claim 5, wherein: Sulfonamide, cyclic diaryliodonium salt, tetraethylcyanocopper hexafluorophosphate, metal-centered chiral cobalt (III) complex anion, and lithium acetate were added to a dry Schlenk tube; after evacuation, nitrogen filling cycle was performed three times, and finally the Schlenk tube was refilled with nitrogen, followed by the addition of dichloromethane.

7. The preparation method according to claim 6, wherein: Dichloromethane is cooled to -12°C to -8°C in advance and then added; after reacting for 34 to 38 hours, the solid part is first filtered out, the reaction liquid is separated, and the axial chiral sulfilimine compound is purified by column chromatography.

8. The preparation method according to claim 5 or 6, wherein: Relative to 0.15mmol of sulfenamide, the amount of cyclic diaryliodonium salt used is 0.08-0.12mmol, the amount of metal-centered chiral cobalt (III) complex anion used is 0.008-0.012mmol, the amount of tetraethylcyanocopper hexafluorophosphate tetrafluoroborate used is 0.008-0.012mmol, the amount of lithium acetate used is 0.20-0.60mmol, and the amount of dichloromethane used is 2.0-4.0mL.

9. Use of the axially chiral sulfilimine compound according to any one of claims 1 to 4 in a biologically active molecular framework.

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