Chiral thioimine ester compound as well as preparation method and application thereof

Abstract

The preparation method comprises the following steps: stirring sulfenamide, isobutanol, # imgabs0 # MS, metal center chiral cobalt (III) complex anions and ultra-dry tetrahydrofuran at the temperature of minus 40 DEG C for 30 minutes, then adding N-iodosuccinimide, reacting at the same temperature for 36 hours, filtering, washing and drying to obtain the chiral sulfur imine ester compound. After the reaction is finished, quenching by using a Na2S2O3 aqueous solution, and separating and purifying to obtain the chiral sulfur imine ester compound. The chiral sulfur imine ester compound prepared by the invention provides a stable and practical method for solving the challenging asymmetry problem in sulfur stereochemistry, and opens up a way for novel chiral sulfur-containing compounds which are widely applied in the fields of medicines and pesticides.

Description

Technical Field

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

[0002] Chiral sulfur compounds are of great significance in asymmetric synthesis and drug discovery. Over the past few years, extensive research has focused on catalytically controlled synthesis of S-chiral compounds. Currently, research on the catalytic synthesis of chiral sulfilimines focuses primarily on constructing sulfur chirality, particularly utilizing transition metal catalysis or organocatalytic strategies to achieve highly enantioselective synthesis of sulfilimines with varying aromatic or alkyl substituents. These breakthroughs not only address key challenges in the synthesis of sulfilimines but also provide important tools for drug discovery and organic synthesis.

[0003] Among the numerous chiral sulfur compounds, chiral sulfimidates, as aza analogs of sulfinates, are universal precursors of various azasulfur stereoisomerization centers. Their azasulfur stereoisomerization centers can provide additional modification sites due to their N-substitution, form more hydrogen bonds, and enhance structural diversity, thereby greatly improving the pharmacological parameters and physicochemical properties of some candidate drugs.

[0004] However, the asymmetric catalytic synthesis of chiral sulfimidates has long been a research challenge in the field of asymmetric catalysis, lacking effective asymmetric catalytic synthesis strategies. In 2023, Japanese chemists achieved the stereospecific synthesis of chiral sulfimidates via asymmetric O-isopropylation of chiral sulfenamides (Angew. Chem. Int. Ed. 2023, 62, e202300637). Recently, Wu Xingxing's group at Guizhou University achieved the asymmetric catalytic synthesis of chiral sulfimidates via dynamic kinetic resolution of racemic sulfenamides (Angew. Chem. Int. Ed. 2025, e202500170). In recent years, sulfur-functionalized sulfenamides have gradually attracted the interest of chemists at home and abroad, providing a new approach for the asymmetric catalytic synthesis of chiral sulfilimines (J.Am.Chem.Soc.2023,145,6310;Org.Lett.2023,25,2830;J.Org.Chem.2023,88,16116.). Therefore, the development of new catalytic strategies for the synthesis of chiral sulfilimines is highly desirable and is expected to advance the development of chiral sulfilimine pesticides and pharmaceuticals. Summary of the Invention

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

[0006] In order to achieve the above object, the present invention provides a chiral sulfilimine lipid compound, the chiral sulfilimine lipid compound has the general structural formula:

[0007]

[0008] Among them, R 1 C 1-8 Straight chain or branched alkyl / cycloalkyl / alkynyl, C3 halogenated straight chain alkyl, C 6-9 One of aryl or substituted aryl, naphthyl;

[0009] The substituted aryl group is C 1-3 One of an alkyl-substituted aryl group, a C2 oxyalkyl-substituted aryl group, a nitro-substituted phenethyl group, a trifluoromethyl-substituted benzyl group or a halogenated benzyl group;

[0010] R 2 is n-butyl or cyclohexyl, C 6-9 one of aryl, benzyl, substituted aryl, substituted benzyl or thienyl;

[0011] The substituted aryl group is one of a methyl or isopropyl substituted aryl group, a cyano substituted aryl group, a methyl formate substituted aryl group, a nitro substituted aryl group, a methoxy substituted aryl group, a trifluoromethyl substituted aryl group or a halogenated aryl group; the substituted benzyl group is a methyl substituted benzyl group;

[0012] R 3 C 3 / 4 / 6 Straight chain or branched alkyl / cycloalkyl, C 6-8 One of substituted aryl, naphthyl, thienyl or 4-methylanilino;

[0013] The substituted aryl group is one of a cyano-substituted aryl group, a trifluoromethyl-substituted aryl group, a nitro-substituted aryl group, a methylformyl-substituted aryl group, a benzoyl-substituted aryl group, a methyl-substituted aryl group, a methoxy-substituted aryl group or a halogenated aryl group.

[0014] In a preferred embodiment of the present invention, the alkyl group is one of methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, 3-pentyl, n-hexyl, n-octyl or β-cholestyl;

[0015] In a preferred embodiment of the present invention, the cycloalkyl group is one of cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclohexyl, cyclopentylethyl or cyclohexylethyl.

[0016] In a preferred embodiment of the present invention, the halogen is one of fluorine, chlorine or bromine.

[0017] The present invention also provides a method for preparing a chiral sulfilimine lipid compound, the preparation method comprising:

[0018] 1) Sulfenamide (Formula 2), alcohol (Formula 3), The metal-centered chiral cobalt (III) complex anion and ultra-dry tetrahydrofuran are mixed and reacted at -45°C to -35°C for 25-35 minutes;

[0019] 2) N-iodosuccinimide is then added, and the entire system is reacted at -45°C to -35°C for 35-37 hours. A Na2S2O3 aqueous solution is added, and the organic layer is separated from the aqueous phase to quench the reaction. The chiral sulfilimine lipid compound (Formula 4) is isolated and purified.

[0020]

[0021] The preparation method of the above-mentioned chiral sulfilimine lipid compounds is to achieve an asymmetric oxidative esterification reaction of sulfenamides by catalyzing a chiral cobalt (III) complex anion sodium salt. This method is applicable to a series of reactions of sulfenamides and alcohols and can produce chiral sulfilimine lipid compounds with extremely high enantioselectivity, regioselectivity and chemoselectivity.

[0022] In a preferred embodiment of the present invention, relative to 0.10 mmol of sulfenamide, the amount of isobutanol is 0.20 mmol, the amount of the metal-centered chiral cobalt (III) complex anion is 0.01 mmol, and the amount of N-iodosuccinimide is 0.20 mmol. The amount of used is 100 mg, and the amount of tetrahydrofuran used is 1.0 mL.

[0023] In the above method, the metal-centered chiral cobalt(III) complex anion catalyst can be prepared using the methods reported in Angew. Chem. Int. Ed. 2015, 54, 11209; Angew. Chem. Int. Ed. 2017, 56, 11931; and ZL201510426983.X. In the above reaction, the enantiomeric excess (ee) of the resulting chiral sulfilimine compound can reach up to 97%.

[0024] The present invention discloses a method for preparing chiral sulfilimine lipid compounds. This method utilizes a metal-centered chiral cobalt (III) complex anion-catalyzed asymmetric S-esterification reaction involving sulfenamide to obtain chiral sulfilimine lipid compounds. The method is simple to operate, employs mild reaction conditions, utilizes readily available and economical raw materials, and exhibits high optical purity (EE values ​​as high as 97%). The chiral sulfilimine lipid compounds prepared by the present invention are expected to find widespread application in asymmetric synthesis, as well as in the research and development of pharmaceuticals 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 detailed description, 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 liquid phase spectrum of compound 4a prepared in Example 1. DETAILED DESCRIPTION

[0028] The following are detailed descriptions of the specific embodiments of the present invention. It should be understood that the specific embodiments described herein are intended only to illustrate and explain the present invention and are not intended to limit the present invention. In the examples, the yield of a 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 Sinopharm. 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: To a 10 mL dry reaction tube, add sulfenamide 2a (0.10 mmol), isobutanol 3a (0.20 mmol), (100 mg), the metal-centered chiral cobalt(III) complex anion Λ-(S,S)-1a (0.01 mmol); ultra-dry tetrahydrofuran (1.0 mL) was added to a reaction tube and stirred at -40°C for 30 minutes. N-iodosuccinimide (0.20 mmol) was then added to the reaction tube in one portion and the entire system was reacted at -40°C for 36 hours. The reaction was quenched by adding aqueous Na2S2O3 solution and then separating the organic layer from the aqueous phase. After quenching the reaction, the aqueous phase was extracted with ethyl acetate (3 × 5.0 mL). The organic layer was dried over anhydrous sodium sulfate. The resulting mixture was filtered and concentrated by vacuum distillation. The reaction mixture was then diluted with 1.0 mL of dichloromethane. Thin-layer silica gel was added to a standard glass column and the dissolved mixture was subjected to nitrogen-pressurized column chromatography (column length, 15 cm, flow rate, 3 drops / second) using a 10:1 (volume ratio) petroleum ether:ethyl acetate as eluent. Purification by flash column chromatography yielded the axially chiral sulfilimine compound 4a in 94% yield and 93% ee. The same applies to compounds 4a-4ca in the following examples. Chiral sulfilimine lipid compounds were obtained through separation and purification.

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

[0034]

[0035] Characterization data of compound 4a:

[0036] isobutyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4a: yield: 94% (33.7mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-108.9 (c 0.73CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.5Hz, 2H), 7.96 (d, J=8.4Hz, 2H), 7.61 (d, J=8.4Hz, 2H), 7.50 (t, J=7.2Hz, 1H), 7.43 (t, J= 7.5Hz, 2H), 4.06 (dd, J=9.5, 6.7Hz, 1H), 3.70 (dd, J=9.5, 6.7Hz, 1H), 2.01-1.88 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.6Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.5, 156.6, 136.2, 133.8, 131.8, 129.6, 128.0, 127.7, 126.6, 74.2, 35.3, 31.2, 28.9, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 28 NO2S: 358.1835, found: 358.1937; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.06min(major), t R =6.60min(minor).

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

[0038]

[0039] The same method as in Example 1 was used to isolate the product 4b with a yield of 98% and ee of 93%.

[0040] The structure of compound 4b is as follows:

[0041]

[0042] Characterization data of compound 4b:

[0043] methyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4b: yield: 98% (31.0mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-200.9 (c 0.23CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.30 (d, J=8.0Hz, 2H), 7.98 (d, J=8.4Hz, 2H), 7.63 (d, J=8. 4Hz, 2H), 7.52 (t, J=7.3Hz, 1H), 7.44 (t, J=7.5Hz, 2H), 3.67 (s, 3H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.6, 157.0, 136.0, 132.8, 131.9, 129.6, 128.1, 127.9, 126.7, 52.8, 35.4, 31.3; HRMS (ESI) m / z: [M+H] + calculated for C 18 H 22 NO2S: 316.1366, found: 316.1368; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =21.39min(major), t R=23.34min(minor).

[0044] Example 3: Synthesis and characterization of compound 4c

[0045]

[0046] The same method as in Example 1 was used to isolate the product 4c with a yield of 92% and ee of 95%.

[0047] The structure of compound 4c is as follows:

[0048]

[0049] Characterization data of compound 4c:

[0050] thyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4c: yield: 92% (30.2mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-198.2 (c 0.17CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.9Hz, 2H), 7.97 (d, J=8.3Hz, 2H), 7.62 (d, J=8.3Hz, 2H), 7.51 (t, J=7.2Hz, 1H), 7. 43 (t, J=7.6Hz, 2H), 4.35 (dq, J=14.3, 7.1Hz, 1H), 4.07 (dq, J=14.5, 7.1Hz, 1H), 1.37 (s, 9H), 1.32 (t, J=7.1Hz, 3H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.7, 136.1, 133.7, 131.9, 129.6, 128.1, 127.7, 126.6, 64.8, 35.3, 31.3, 15.8; HRMS (ESI) m / z: [M+H] + calculated for C 19 H 24NO2S: 330.1522, found: 330.1530; Enantiomeric excess: 95%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =16.54min(major), t R =19.35min(minor).

[0051] Example 4: Synthesis and characterization of compound 4d

[0052]

[0053] The same method as in Example 1 was used to isolate the product 4d with a yield of 94% and ee of 90%.

[0054] The structure of compound 4d is as follows:

[0055]

[0056] Characterization data of compound 4d:

[0057] propyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4d: yield: 94% (32.4mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-198.2 (c 0.29 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.32-8.26 (m, 2H), 7.97 (d, J=8.4Hz, 2H), 7.62 (d, J=8.4Hz, 2H), 7.51 (t, J=7.3Hz, 1H), 7.43 (t, J=7.6Hz, 2H), 4.24 (dt, J=9.7, 6.7Hz, 1H), 3.92 (dt, J=9.8, 6.7Hz, 1H), 1.69 (dt, J=14.1, 7.2Hz, 2H), 1.37 (s, 9H), 0.90 (t, J=7.4Hz, 3H); 13C NMR (151MHz, CDCl3) δ178.6, 156.7, 136.2, 133.8, 131.8, 129.6, 128.1, 127.7, 126.6, 70.1, 35.3, 31.3, 23.3, 10.4; HRMS (ESI) m / z: [M+Na] + calculated for C 20 H 25 NNaO2S: 366.1498, found: 366.1504; Enantiomericexcess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.14min(major), t R =11.25min(minor).

[0058] Example 5: Synthesis and characterization of compound 4e

[0059]

[0060] The same method as in Example 1 was used to isolate the product 4e with a yield of 95% and ee of 89%.

[0061] The structure of compound 4e is as follows:

[0062]

[0063] Characterization data of compound 4e:

[0064] hexyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4e: yield: 95% (36.7mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-52.0 (c 0.03CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.29 (d, J=7.9Hz, 2H), 7.96 (d, J=8.4Hz, 2H), 7.61 (d, J=8.4Hz, 2H), 7.50 (t, J=7.3Hz, 1H), 7.43 (t, J=7.6Hz, 2H), 4.27 (d t, J=9.7, 6.7Hz, 1H), 3.95 (dt, J=9.7, 6.7Hz, 1H), 1.67-1.63 (m, 2H), 1. 37(s, 9H), 1.33-1.28(m, 2H), 1.27-1.21(m, 4H), 0.83(t, J=6.9Hz, 3H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.7, 136.2, 133.8, 131.8, 129.6, 128.1, 127.7 , 126.6, 68.5, 35.3, 31.4, 31.3, 29.9, 25.4, 22.6, 14.1; HRMS (ESI) m / z: [M+Na] + calculated for C 23 H 31 NNaO2S: 408.1968, found: 408.1975; Enantiomeric excess: 89%, determined by HPLC (Daicel Chiralpak OD, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.37min(major), t R =8.13min(minor).

[0065] Example 6: Synthesis and Characterization of Compound 4f

[0066]

[0067] The same method as in Example 1 was used to isolate the product 4f with a yield of 96% and ee of 86%.

[0068] The structure of compound 4f is as follows:

[0069]

[0070] Characterization data of compound 4f:

[0071] octyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4f: yield:96%(39.7mg);flash column chromatography eluent,petroleum ether / ethyl acetate=10:1;colorless oil;[α] D 20 =-172.1(c 0.19CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.30(dd,J=8.0,1.0Hz,2H),7.97(d,J=8.6Hz,2H),7.61(d,J=8.6Hz,2H),7.53-7.48(m,1H),7.43(t,J=7.6Hz,2H),4.27(dt,J=9.9,6.6Hz,1H),3.94(dt,J=9.9,6.6Hz,1H),1.67-1.62(m,2H),1.37(s,9H),1.32-1.27(m,2H),1.26-1.18(m,8H),0.85(t,J=7.1Hz,3H); 13 C NMR(151MHz,CDCl3)δ178.5,156.6,136.1,133.7,131.8,129.6,128.0,127.7,126.6,68.4,35.3,31.8,31.2,29.9,29.2,29.2,25.7,22.7,14.2;HRMS(ESI)m / z:[M+Na] + calculatedfor C 25 H 35 NNaO2S:436.2281,found:436.2286;Enantiomeric excess:86%,determined byHPLC(Daicel Chiralpak AD,isopropanol / hexane=10 / 90,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =6.93min(major),t R =6.16min(minor).

[0072] Example 7: Synthesis and characterization of compound 4g

[0073]

[0074] The same method as in Example 1 was used to finally separate 4 g of the product with a yield of 92% and ee of 92%.

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

[0076]

[0077] Characterization data of compound 4g:

[0078] isopropyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4g: yield: 92% (31.5mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-215.9 (c 0.04CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28 (d, J=7.4Hz, 2H), 7.96 (d, J=8.4Hz, 2H), 7.60 (d, J=8.4Hz, 2H), 7.49 (t, J=7.3Hz, 1H) , 7.42 (t, J=7.5Hz, 2H), 5.07 (dt, J=12.5, 6.3Hz, 1H), 1.46 (d, J=6.1Hz, 3H), 1.37 (s, 9H), 1.28 (d, J=6.2Hz, 3H); 13 C NMR (151MHz, CDCl3) δ178.8, 156.5, 136.1, 134.6, 131.8, 129.6, 128.1, 127.5, 126.6, 76.3, 35.3, 31.3, 23.9, 23.5; HRMS (ESI) m / z: [M+Na] + calculated for C 20 H 25 NNaO2S: 366.1498, found: 366.1505; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =12.14min(major), t R =14.58min(minor).

[0079] Example 8: Synthesis and characterization of compound 4h

[0080]

[0081] The same method as in Example 1 was used to finally separate the product 4h with a yield of 92% and ee of 87%.

[0082] The structure of compound 4h is as follows:

[0083]

[0084] Characterization data of compound 4h:

[0085] pentan-3-yl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4h: yield: 92% (34.1mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-124.9 (c 0.29 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.27 (d, J=7.1Hz, 2H), 7.97 (d, J=8.5Hz, 2H), 7.60 (d, J=8.5Hz, 2H), 7.49 (t, J=7.3Hz, 1H), 7.42 (t, J=7. 4Hz, 2H), 4.82-4.74 (m, 1H), 1.84-1.75 (m, 2H), 1.65-1.52 (m, 2H), 1.36 (s, 9H), 0.99 (t, J=7.4Hz, 3H), 0.87 (t, J=7.4Hz, 3H); 13 C NMR (151MHz, CDCl3) δ178.7, 156.4, 136.3, 135.0, 131.7, 129.5, 128.0, 127.4, 126.5, 86.2, 35.3, 31.3, 27.9, 27.2, 9.6, 9.4; HRMS (ESI) m / z: [M+H] + calculated for C 27 H 30NO2S: 372.1992, found: 372.1928; Enantiomeric excess: 87%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95 flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.79min(major), t R =11.46min(minor).

[0086] Example 9: Synthesis and Characterization of Compound 4i

[0087]

[0088] The same method as in Example 1 was used to isolate the product 4i with a yield of 95% and ee of 92%.

[0089] The structure of compound 4i is as follows:

[0090]

[0091] Characterization data of compound 4i:

[0092] cyclobutyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4i: yield: 95% (33.7mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-209.3 (c 0.27CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28 (d, J=7.1Hz, 2H), 7.97 (d, J=8.5Hz, 2H), 7.61 (d, J=8.5Hz, 2H), 7.50 (t, J=7.3Hz, 1H), 7.42 (t, J=7.6Hz, 2H), 5.00 (p , J=7.6Hz, 1H), 2.43-2.36(m, 1H), 2.25-2.18(m, 1H), 2.18-2.12(m, 1H) , 2.12-2.05(m, 1H), 1.76-1.69(m, 1H), 1.54-1.48(m, 1H), 1.37(s, 9H); 13C NMR (151MHz, CDCl3) δ178.5, 156.7, 136.2, 134.0, 131.8, 129.6, 128.1, 127.7, 126.6, 73.3, 35.3, 32.4, 31.9, 31.3, 13.3; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 26 NO2S: 356.1679, found: 356.1683; HRMS (ESI) m / z: [M+H] + calculated for C 27 H 30 NO2S: 372.1992, found: 372.1928; Enantiomeric excess: 92%, determined by HPLC (Daicel ChiralpakIF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =8.53min(major), t R =9.45min(minor).

[0093] Example 10: Synthesis and characterization of compound 4j

[0094]

[0095] The same method as in Example 1 was used to isolate product 4j with a yield of 91% and ee of 86%.

[0096] The structure of compound 4j is as follows:

[0097]

[0098] Characterization data of compound 4.j:

[0099] cyclohexyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4j: yield: 91% (34.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-147.1 (c 0.05CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.32-8.25 (m, 2H), 7.95 (dd, J=8.6, 1.9Hz, 2H), 7.60 (dd, J=8 .6, 1.8Hz, 2H), 7.51-7.46 (m, 1H), 7.44-7.39 (m, 2H), 4.81 (dd, J=10.9, 7.3Hz, 1H), 2.19-2.11(m, 1H), 1.94-1.87(m, 1H), 1.82-1.68(m, 2H), 1.63(dd, J=21.7, 10.5Hz , 1H), 1.54-1.49(m, 1H), 1.49-1.41(m, 2H), 1.40-1.34(m, 10H), 1.28-1.21(m, 1H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.4, 136.2, 134.8, 131.7, 129.5, 128.0, 127.4 , 126.5, 81.1, 53.6, 35.2, 33.6, 33.1, 31.1, 25.2, 23.8; HRMS (ESI) m / z: [M+Na] + calculated for C 23 H 29 NNaO2S: 406.1811, found: 406.1818; Enantiomeric excess: 86%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =12.88min(major), t R =14.01min(minor).

[0100] Example 11: Synthesis and Characterization of Compound 4k

[0101]

[0102] The same method as in Example 1 was used to finally separate the product 4k with a yield of 97% and ee of 91%.

[0103] The structure of compound 4k is as follows:

[0104]

[0105] Characterization data of compound 4k:

[0106] cyclopropylmethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4k:yield:97%(34.6mg);flash column chromatography eluent,petroleum ether / ethylacetate=10:1;colorless oil;[α] D 20 =-174.0(c 0.32CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.28(d,J=7.7Hz,2H),7.99(d,J=8.5Hz,2H),7.61(d,J=8.5Hz,2H),7.50(t,J=7.3Hz,1H),7.42(t,J=7.6Hz,2H),4.15(dd,J=10.8,7.7Hz,1H),3.90(dd,J=10.8,7.2Hz,1H),1.37(s,9H),1.21-1.13(m,1H),0.64-0.54(m,2H),0.39-0.32(m,1H),0.28-0.22(m,1H); 13 CNMR(151MHz,CDCl3)δ178.6,156.6,136.1,134.0,131.8,129.6,128.1,127.7,126.6,74.3,35.3,31.3,11.2,4.2,3.8;HRMS(ESI)m / z:[M+H] + calculated for C 21 H 26 NO2S:356.1679,found:356.1684;Enantiomeric excess:91%,determined by HPLC(Daicel ChiralpakIF,isopropanol / hexane=20 / 80,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =8.81min(major),t R =9.75min(minor).

[0107] Example 12: Synthesis and characterization of compound 41

[0108]

[0109] The same method as in Example 1 was used to isolate the product 41 with a yield of 90% and ee of 85%.

[0110] The structure of compound 41 is as follows:

[0111]

[0112] Characterization data of compound 41:

[0113] 2-cyclopentylethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate4l: yield: 90% (35.9mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-155.9 (c 0.37CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.6Hz, 2H), 7.97 (dd, J=8.4, 1.6Hz, 2H), 7.61 (dd, J=8.4, 1.6Hz, 2H), 7.50 (dd, J=7.4, 5.9Hz, 1H), 7.43 (t, J=6.8Hz, 2H), 4 .32-4.23(m, 1H), 3.99-3.89(m, 1H), 1.82-1.76(m, 1H), 1.73-1.62(m, 4H), 1. 57-1.51 (m, 2H), 1.49-1.42 (m, 2H), 1.36 (d, J=1.9Hz, 9H), 1.07-0.96 (m, 2H); 13 C NMR (151MHz, CDCl3) δ178.5, 156.7, 136.2, 133.8, 131.8, 129.6, 128.0, 127.7, 1 26.6, 67.8, 36.5, 36.0, 35.3, 32.6, 32.5, 31.2, 25.1, 25.1; HRMS (ESI) m / z: [M+H] + calculated for C 24 H 32NO2S: 398.2148, found: 398.2156; Enantiomericexcess: 85%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =5.32min(major), t R =4.90min(minor).

[0114] Example 13: Synthesis and Characterization of Compound 4m

[0115]

[0116] The same method as in Example 1 was used to isolate the product 4m with a yield of 98% and ee of 84%.

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

[0118]

[0119] Characterization data of compound 4m:

[0120] 2-cyclohexylethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4m: yield: 98% (40.4mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-153.9 (c 0.33CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.33-8.26 (m, 2H), 7.97 (d, J=8.5Hz, 2H), 7.61 (d, J=8.5Hz, 2H), 7.50 (t, J=7.3Hz, 1H), 7.43 (t, J=7.6Hz, 2H), 4.29 (dt , J=10.0, 6.7Hz, 1H), 3.96 (dt, J=10.0, 6.7Hz, 1H), 1.66-1.51 (m, 7H), 1.37(s, 9H), 1.34-1.30(m, 1H), 1.20-1.05(m, 3H), 0.89-0.78(m, 2H); 13C NMR (126MHz, CDCl3) δ178.5, 156.7, 136.2, 133.7, 131.8, 129.6, 128.0, 127.7, 126. 6, 66.2, 37.2, 35.3, 34.1, 33.2, 33.1, 31.3, 26.5, 26.2, 26.2; HRMS (ESI) m / z: [M+Na] + calculated for C 25 H 33 NNaO2S: 434.2124, found: 434.2128; Enantiomeric excess: 84%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =5.18min(major), t R =4.65min(minor).

[0121] Example 14: Synthesis and Characterization of Compound 4n

[0122]

[0123] The same method as in Example 1 was used to isolate the product 4n with a yield of 94% and an ee of 94%.

[0124] The structure of compound 4n is as follows:

[0125]

[0126] Characterization data of compound 4n:

[0127] benzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4n: yield: 94% (36.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-160.0 (c 0.22CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.33 (dd, J=8.0, 1.0Hz, 2H), 7.94 (d, J=8.7Hz, 2H), 7.59 (d, J=8.6Hz, 2H), 7.55-7.51 (m , 1H), 7.46 (t, J=7.5Hz, 2H), 7.41-7.25 (m, 5H), 5.36 (d, J=11.5Hz, 1H), 4.98 (d, J=11.5Hz, 1H), 1.36 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.7, 156.8, 136.0, 135.7, 133.5, 131.9, 129.6, 129. 0, 128.8, 128.7, 128.1, 127.8, 126.6, 70.1, 35.3, 31.3; HRMS (ESI) m / z: [M+H] + calculated for C 24 H 26 NO2S: 392.1679, found: 392.1688; Enantiomeric excess: 94%, determined by HPLC (Daicel Chiralpak IG, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.51min(major), t R =12.89min(minor).

[0128] Example 15: Synthesis and characterization of compound 4o

[0129]

[0130] The same method as in Example 1 was used to isolate the product 4o with a yield of 94% and an ee of 94%.

[0131] The structure of compound 4o is as follows:

[0132]

[0133] Characterization data of compound 4o:

[0134] phenethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4o:yield:94%(38.0mg);flash column chromatography eluent,petroleum ether / ethyl acetate=10:1;colorless oil;[α] D 20 =-203.8(c 0.28CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.31(d,J=8.1Hz,2H),7.81(d,J=8.3Hz,2H),7.56-7.50(m,3H),7.44(t,J=7.6Hz,2H),7.27(dd,J=11.0,4.1Hz,2H),7.22(dd,J=10.6,3.9Hz,1H),7.16(d,J=7.6Hz,2H),4.50(dt,J=10.0,7.0Hz,1H),4.17(dt,J=10.1,7.0Hz,1H),3.01-2.94(m,2H),1.36(s,9H); 13 C NMR(151MHz,CDCl3)δ178.6,156.6,137.2,136.0,133.3,131.9,129.6,129.2,128.6,128.0,127.7,126.7,126.5,68.8,36.4,35.2,31.2;HRMS(ESI)m / z:[M+Na] + calculated forC 25 H 27 NNaO2S:428.1655,found:428.1655;Enantiomeric excess:94%,determined byHPLC(Daicel Chiralpak IF,isopropanol / hexane=5 / 95,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =21.16min(major),t R =23.75min(minor).

[0135] Example 16: Synthesis and Characterization of Compound 4p

[0136]

[0137] The same method as in Example 1 was used to isolate the product 4p with a yield of 98% and ee of 91%.

[0138] The structure of compound 4p is as follows:

[0139]

[0140] Characterization data of compound 4p:

[0141] 3-phenylpropyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4p: yield: 98% (41.3mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-173.0 (c 0.24CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.31 (d, J=7.4Hz, 2H), 7.98 (d, J=8.3Hz, 2H), 7.62 (d, J=8.4Hz, 2H), 7.52 (t, J=7.3Hz, 1H), 7.44 (t, J=7.5Hz, 2H), 7.21 (t, J=7. 4Hz, 2H), 7.15 (t, J=7.3Hz, 1H), 7.10 (d, J=7.4Hz, 2H), 4.31-4.25 (m, 1H), 3.97-3.91(m, 1H), 2.66(t, J=7.6Hz, 2H), 2.00-1.94(m, 2H), 1.38(s, 9H); 13 C NMR (151MHz, CDCl3) δ178.5, 156.8, 141.0, 136.1, 133.5, 131.9, 129.6, 128.54, 128. 48, 128.1, 127.7, 126.6, 126.1, 67.0, 35.3, 31.9, 31.5, 31.3; HRMS (ESI) m / z: [M+Na] + calculated for C 26 H 29NNaO2S: 442.1811, found: 442.1815; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =21.84min(major), t R =23.96min(minor).

[0142] Example 17: Synthesis and Characterization of Compound 4q

[0143]

[0144] The same method as in Example 1 was used to isolate the product 4q with a yield of 90% and ee of 93%.

[0145] The structure of compound 4q is as follows:

[0146]

[0147] Characterization data of compound 4q:

[0148] 2-phenoxyethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4q: yield: 90% (37.8mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-258.1 (c 0.04CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.8Hz, 2H), 8.01 (d, J=8.5Hz, 2H), 7.59 (d, J=8.5Hz, 2H), 7.51 (t, J=7.1Hz, 1H), 7.44 (t, J=7.5Hz, 2H), 7.26 (t, J= 7.9Hz, 2H), 6.95 (t, J=7.3Hz, 1H), 6.86 (d, J=8.1Hz, 2H), 4.77-4.71 (m, 1 H), 4.40-4.33(m, 1H), 4.26-4.20(m, 1H), 4.19-4.13(m, 1H), 1.36(s, 9H); 13C NMR (126MHz, CDCl3) δ178.8, 158.4, 156.9, 135.9, 133.5, 132.0, 129.6, 128. 1, 127.8, 126.6, 121.3, 114.7, 67.3, 66.7, 35.3, 31.2; HRMS (ESI) m / z: [M+Na] + calculated for C 25 H 27 NNaO3S: 444.1604, found: 444.1609; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak OJ, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.73min(major), t R =9.10min(minor).

[0149] Example 18: Synthesis and Characterization of Compound 4r

[0150]

[0151] The same method as in Example 1 was used to isolate the product 4r with a yield of 95% and ee of 93%.

[0152] The structure of compound 4r is as follows:

[0153]

[0154] Characterization data of compound 4r:

[0155] 4-fluorobenzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4r: yield: 95% (38.9mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-191.5 (c 0.06CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.32 (d, J=7.4Hz, 2H), 7.93 (d, J=8.4Hz, 2H), 7.60 (d, J=8.5Hz, 2H), 7.53 (t, J=7.3Hz, 1H), 7.46 (t, J= 7.6Hz, 2H), 7.31 (dd, J=8.3, 5.5Hz, 2H), 7.00 (t, J=8.6Hz, 2H), 5.30 (d, J=11.5Hz, 1H), 4.95 (d, J=11.5Hz, 1H), 1.36 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.7, 163.0 (d, J=247.7Hz), 156.9, 135.9, 133.4, 132.0, 131.6 (d, J=3.4Hz), 131. 0 (d, J=8.5Hz), 129.6, 128.2, 127.8, 126.7, 115.7 (d, J=21.6Hz), 69.2, 35.3, 31.3; HRMS (ESI) m / z: [M+Na] + calculated for C 24 H 24 FNO2S: 432.1404, found: 432.1411; 19 F NMR (565MHz, CDCl3) δ-112.80; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak ID, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =8.75min(major), t R =8.24min(minor).

[0156] Example 19: Synthesis and Characterization of Compound 4s

[0157]

[0158] The same method as in Example 1 was used to isolate the product 4s with a yield of 93% and ee of 91%.

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

[0160]

[0161] Characterization data of compound 4s:

[0162] 4-chlorobenzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4s: yield: 93% (39.5mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-191.0 (c 0.11 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.31 (d, J=7.9Hz, 2H), 7.93 (d, J=8.3Hz, 2H), 7.60 (d, J=8.4Hz, 2H), 7.52 (dd, J=10.7, 3.8H z, 1H), 7.45 (t, J=7.6Hz, 2H), 7.27 (q, J=8.3Hz, 4H), 5.28 (d, J=11.7Hz, 1H), 4.93 (d, J=11.7Hz, 1H), 1.36 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.7, 157.0, 135.8, 134.7, 134.3, 133.3, 132.0, 130.3 , 129.6, 128.9, 128.2, 127.8, 126.7, 68.9, 35.3, 31.2; HRMS (ESI) m / z: [M+Na] + calculated for C 20 H 24 ClNNaO2S: 448.1108, found: 448.1110; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak ID, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.49min(major), t R =8.82min(minor).

[0163] Example 20: Synthesis and Characterization of Compound 4t

[0164]

[0165] The same method as in Example 1 was used to finally separate the product 4t with a yield of 97% and ee of 94%.

[0166] The structure of compound 4t is as follows:

[0167]

[0168] Characterization data of compound 4t:

[0169] 4-bromobenzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4t: yield: 97% (45.7mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-16.3 (c 2.1 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.31 (d, J=7.3Hz, 2H), 7.94 (d, J=8.3Hz, 2H), 7.60 (d, J=8.3Hz, 2H), 7.52 (t, J=7.2Hz, 1H), 7.45 (dd, J=13.3, 7.7Hz, 4H), 7.19 (d, J=8.0Hz, 2H), 5.27 (d, J=11.8Hz, 1H), 4.92 (d, J=11.8Hz, 1H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.9, 135.8, 134.7, 133.2, 132.0, 131.8, 130.5 , 129.6, 128.1, 127.7, 126.6, 122.8, 68.8, 35.3, 31.2; HRMS (ESI) m / z: [M+Na] + calculated for C 24 H 24 BrNNaO2S: 492.0603, found: 492.0602; Enantiomeric excess: 94%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =8.29min(major), t R =7.78min(minor).

[0170] Example 21: Synthesis and Characterization of Compound 4u

[0171]

[0172] The same method as in Example 1 was used to isolate the product 4u with a yield of 96% and ee of 94%.

[0173] The structure of compound 4u is as follows:

[0174]

[0175] Characterization data of compound 4u:

[0176] 4-(trifluoromethyl)benzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4u: yield: 96% (44.0mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-31.1(c0.27CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.35-8.27 (m, 2H), 7.97 (d, J=8.5Hz, 2H), 7.61 (d, J=8.5Hz, 2H), 7.59-7.51 ( m, 3H), 7.44 (dd, J=17.6, 8.0Hz, 4H), 5.35 (d, J=12.1Hz, 1H), 5.02 (d, J=12.1Hz, 1H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.8, 157.2, 139.8, 135.7, 133.2, 132.1, 129.7, 128.8, 128.2, 127.8, 126.8, 125.6 (q, J=3.9Hz), 68.4, 35.4, 31.2; 19 FNMR (565MHz, CDCl3) δ-62.69; HRMS (ESI) m / z: [M+Na] + calculated for C 25 H 24F3NNaO2S: 482.1372, found: 482.1377; Enantiomeric excess: 94%, determined by HPLC (DaicelChiralpak ID, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.47min(major), t R =6.86min(minor).

[0177] Example 22: Synthesis and Characterization of Compound 4v

[0178]

[0179] The same method as in Example 1 was used to isolate the product 4v with a yield of 94% and ee of 92%.

[0180] The structure of compound 4v is as follows:

[0181]

[0182] Characterization data of compound 4v:

[0183] 3-methylbenzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4v: yield: 94% (38.1mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-122.4 (c 0.09 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.32 (d, J=7.7Hz, 2H), 7.93 (d, J=8.3Hz, 2H), 7.59 (d, J=8.3Hz, 2H), 7.52 (t, J=7.3Hz, 1H), 7.45 (t, J=7.6 Hz, 2H), 7.22 (t, J=7.4Hz, 1H), 7.12 (d, J=8.3Hz, 3H), 5.31 (d, J=11.4Hz, 1H), 4.93 (d, J=11.4Hz, 1H), 2.31 (s, 3H), 1.36 (s, 9H); 13C NMR (151MHz, CDCl3) δ178.7, 156.8, 138.4, 136.1, 135.6, 133.7, 131.9, 129.8, 129.7, 1 29.6, 128.7, 128.1, 127.9, 126.6, 126.1, 70.3, 35.3, 31.3, 21.5; HRMS (ESI) m / z: [M+Na] + calculated for C 25 H 27 NNaO2S: 428.1655, found: 428.1656; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IG, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.74min(major), t R =12.85min(minor).

[0184] Example 23: Synthesis and characterization of compound 4w

[0185]

[0186] The same method as in Example 1 was used to finally separate the product 4w with a yield of 92% and ee of 93%.

[0187] The structure of compound 4w is as follows:

[0188]

[0189] Characterization data of compound 4w:

[0190] 3,5-dimethylbenzyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate4w: yield: 92% (38.6mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-105.1 (c 0.07CH2Cl2); 1H NMR (600MHz, CDCl3) δ 8.37-8.30 (m, 2H), 7.95 (d, J = 8.5Hz, 2H), 7.60 (d, J = 8.5Hz, 2H), 7.55-7.51 (m, 1H), 7.46 (t , J=7.7Hz, 2H), 6.94 (d, J=5.5Hz, 3H), 5.27 (d, J=11.3Hz, 1H), 4.90 (d, J=11.3Hz, 1H), 2.27 (s, 6H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.7, 138.3, 136.1, 135.4, 133.5, 131.9, 130.5, 1 29.6, 128.1, 127.8, 126.9, 126.6, 70.2, 35.3, 31.2, 21.3; HRMS (ESI) m / z: [M+Na] + calculated for C 26 H29NNaO2S: 442.1811, found: 442.1816; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak IG, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.04min(major), t R =10.82min(minor).

[0191] Example 24: Synthesis and Characterization of Compound 4x

[0192]

[0193] The same method as in Example 1 was used to finally separate the product 4x with a yield of 78% and ee of 92%.

[0194] The structure of compound 4x is as follows:

[0195]

[0196] Characterization data of compound 4x:

[0197] naphthalen-1-ylmethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate4x:yield:78%(34.4mg);flash column chromatography eluent,petroleum ether / ethyl acetate=10:1;colorless oil;[α] D 20 =-108.2(c 0.2CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.38(dd,J=8.3,1.3Hz,2H),8.02(dd,J=5.4,4.3Hz,1H),7.88-7.81(m,4H),7.56-7.47(m,8H),7.41(dd,J=8.2,7.1Hz,1H),5.81(d,J=11.6Hz,1H),5.50(d,J=11.6Hz,1H),1.33(s,9H); 13 C NMR(151MHz,CDCl3)δ178.8,156.7,136.1,133.9,133.5,132.0,131.8,131.4,130.1,129.7,128.8,128.7,128.2,127.8,126.8,126.5,126.2,125.3,124.0,68.8,35.3,31.2;HRMS(ESI)m / z:[M+Na] + calculated for C 28 H 27 NNaO2S:464.1655,found:464.1658;Enantiomeric excess:92%,determined by HPLC(DaicelChiralpak ID,isopropanol / hexane=30 / 70,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =9.34min(major),t R =10.37min(minor).

[0198] Example 25: Synthesis and Characterization of Compound 4y

[0199]

[0200] The same method as in Example 1 was used to isolate the product 4y with a yield of 89% and ee of 92%.

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

[0202]

[0203] Characterization data of compound 4y:

[0204] 4-nitrophenethyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4y: yield: 89% (40.0mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-155.3 (c 0.4CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.24 (d, J=8.1Hz, 2H), 8.07 (d, J=8.2Hz, 2H), 7.83 (d, J=8.3Hz, 2H), 7.56 (d, J=8.3Hz, 2H), 7.54-7.49 (m, 1H), 7.43 (t, J=7.6Hz, 2H), 7.30 (d, J=8.4Hz, 2H), 4.48 (dt, J=10.6, 6.4Hz, 1H), 4.20 (dt, J=10.6, 6.4Hz, 1H), 3.04 (t, J=6.4Hz, 2H), 1.36 (s, 9H); 13 H MS(ESI)m / z:[M+Na] + calculated for C 25 H 26 N2NaO4S: 473.1505, found: 473.1508; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): tR =17.13min(major), t R =16.01min(minor).

[0205] Example 26: Synthesis and Characterization of Compound 4z

[0206]

[0207] The same method as in Example 1 was used to isolate the product 4z with a yield of 75% and ee of 97%.

[0208] The structure of compound 4z is as follows:

[0209]

[0210] Characterization data of compound 4z:

[0211] 3,3,3-trifluoropropyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate4z: yield: 75% (29.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-64.2 (c 0.04CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28 (d, J=7.1Hz, 2H), 7.98 (d, J=8.6Hz, 2H), 7.63 (d, J=8.6Hz, 2H), 7.52 (t, J=7.3Hz, 1H), 7 .44 (t, J=7.6Hz, 2H), 4.50 (dt, J=11.2, 6.4Hz, 1H), 4.21 (dt, J=11.2, 6.4Hz, 1H), 2.57-2.44 (m, 2H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.8, 157.2, 135.6, 132.9, 132.2, 129.6, 128.2, 127.7, 1 26.8, 126.5 (q, J=236.1Hz), 61.0 (q, J=3.6Hz), 35.4, 34.6 (q, J=29.1Hz), 31.2; 19 F NMR(565MHz, CDCl3)δ-64.62; HRMs(EsI)m / z: [M+Na] +calculated for C 20 H 22 F3NNaO3S: 420.1216, found: 420.1219; Enantiomericexcess: 97%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =8.78min(major), t R =9.77min(minor).

[0212] Example 27: Synthesis and Characterization of Compound 4aa

[0213]

[0214] The same method as in Example 1 was used to isolate the product 4aa with a yield of 87% and ee of 93%.

[0215] The structure of compound 4aa is as follows:

[0216]

[0217] Characterization data of compound 4aa:

[0218] 4-fluorobutyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4aa: yield: 87% (31.3mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-570.6 (c 0.02CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.29 (d, J=7.3Hz, 2H), 7.98 (d, J=8.5Hz, 2H), 7.63 (d, J=8.5Hz, 2H), 7.51 (t, J=7.3Hz, 1H), 7.44 (t, J=7.6Hz, 2H), 4.55-4 .50 (m, 1H), 4.48-4.43 (m, 1H), 4.39 (dt, J=10.3, 6.2Hz, 1H), 4.06 (dt, J=10.4, 6.1Hz, 1H), 2.10-1.98(m, 2H), 1.37(s, 9H), 1.35-1.24(m, 2H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.9, 135.9, 133.3, 131.9, 129.6, 128.1, 127.7, 126.7, 80.3 (d, J = 165.4Hz), 63.5 (d, J = 5.1Hz), 35.3, 31.2.30.9 (d, J = 20.0Hz); 19 F NMR(376MHz, CDCl3)δ-222.36--222.81(m); HRMS(ESI)m / z: [M+Na] + calculated for C 20 H 24 FNNaO2S: 384.1404, found: 384.1412; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak OD, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =12.18min(major), t R =13.36min(minor).

[0219] Example 28: Synthesis and Characterization of Compound 4ab

[0220]

[0221] The same method as in Example 1 was used to isolate the product 4ab with a yield of 98% and ee of 93%.

[0222] The structure of compound 4ab is as follows:

[0223]

[0224] Characterization data of compound 4ab:

[0225] 3-chloropropyl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4ab: yield: 98% (37.2mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-193.8 (c 0.06CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.32-8.24 (m, 2H), 8.02-7.95 (m, 2H), 7.65-7.62 (m, 2H), 7.53-7.50 (m, 1H), 7.44 (t, J=7.6 Hz, 2H), 4.40 (dt, J=10.4, 5.9Hz, 1H), 4.11-4.04 (m, 1H), 3.57 (t, J=6.3Hz, 2H), 2.11-2.06 (m, 2H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.6, 157.0, 135.9, 133.2, 132.0, 129.6, 128.1, 127.7, 126.7, 64.1, 41.0, 35.4, 32.6, 31.3; HRMS (ESI) m / z: [M+H] + calculated for C 20 H 25 ClNO2S: 378.1289, found: 378.1298; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak OD, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =12.80min(major), t R =14.25min(minor).

[0226] Example 29: Synthesis and Characterization of Compound 4ac

[0227]

[0228] The same method as in Example 1 was used to isolate the product 4ac with a yield of 96% and ee of 91%.

[0229] The structure of compound 4ac is as follows:

[0230]

[0231] Characterization data of compound 4ac:

[0232] but-3-yn-1-yl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4ac: yield: 96% (34.1mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-214.1 (c 0.29 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.30-8.26 (m, 2H), 8.04-8.00 (m, 2H), 7.65-7.61 (m, 2H), 7.52 (t, J=7.3Hz, 1H), 7.44 (t, J=7.6Hz, 2H), 4.45 (dt, J=10.1, 6.8Hz, 1H), 4.10 (dt, J=10.1, 6.6Hz, 1H), 2.64-2.53 (m, 2H), 2.00 (t, J=2.6Hz, 1H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.7, 156.9, 135.8, 133.3, 132.0, 129.6, 128.1, 127.8, 126.7, 79.9, 70.6, 66.3, 35.3, 31.3, 20.4; HRMS (ESI) m / z: [M+Na] + calculated for C 21 H 23 NNaO2S: 376.1342, found: 376.1346; Enantiomericexcess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.29min(major), t R =8.04min(minor).

[0233] Example 30: Synthesis and characterization of compound 4ad

[0234]

[0235] The same method as in Example 1 was used to isolate the product 4ad with a yield of 93% and an ee of 95%.

[0236] The structure of compound 4ad is as follows:

[0237]

[0238] Characterization data of compound 4ad:

[0239] pent-4-yn-1-yl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4ad: yield: 93% (34.1mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-127.1 (c 0.37 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.1Hz, 2H), 7.98 (d, J=8.5Hz, 2H), 7.62 (d, J=8.5Hz, 2H), 7.51 (t, J=7.3Hz, 1H), 7.43 (t, J=7.7H z, 2H), 4.38 (dt, J=10.2, 6.2Hz, 1H), 4.05 (dt, J=10.2, 6.0Hz, 1H), 2.26 (td, J=7.0, 2.6Hz, 2H), 1.94-1.80 (m, 3H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl3) δ178.7, 156.9, 135.8, 133.3, 132.0, 129.6, 128.1, 127.8, 126.7, 79.9, 70.6, 66.3, 35.3, 31.3, 20.4; HRMS (ESI) m / z: [M+Na] + calculated for C 22 H 25NNaO2S: 390.1498, found: 390.1503; Enantiomeric excess: 95%, determined by HPLC (Daicel Chiralpak OD, isopropanol / hexane=5 / 95, flow rate=0.5mL / min, T=30°C, λ=254nm): t R =22.19min(major), t R =25.51min(minor).

[0240] Example 31: Synthesis and Characterization of Compound 4ae

[0241]

[0242] The same method as in Example 1 was used to isolate the product 4ae with a yield of 74% and ee of 87%.

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

[0244]

[0245] Characterization data of compound 4ae:

[0246] but-2-yn-1-yl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4ae: yield: 74% (26.1mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-156.0 (c 0.03CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28 (d, J=7.4Hz, 2H), 8.02 (d, J=8.5Hz, 2H), 7.62 (d, J=8.5Hz, 2H), 7.51 (t, J=7.3 Hz, 1H), 7.43 (t, J=7.6Hz, 2H), 5.05-5.00 (m, 1H), 4.66-4.61 (m, 1H), 1.83 (t, J=2.2Hz, 3H), 1.37 (s, 9H); 13C NMR (151MHz, CDCl3) δ178.7, 156.9, 135.8, 133.3, 132.0, 129.6, 128.1, 127.9, 126.6, 85.8, 76.8, 73.8, 57.6, 35.3, 31.3, 4.0; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 24 NO2S: 354.1528, found: 354.1530; Enantiomeric excess: 87%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =13.09min(major), t R =14.04min(minor).

[0247] Example 32: Synthesis and Characterization of Compound 4af

[0248]

[0249] The same method as in Example 1 was used to isolate the product 4af with a yield of 92%.

[0250] The structure of compound 4af is as follows:

[0251]

[0252] Characterization data of compound 4af:

[0253] (3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl(R)-N-benzoyl-4-(tert-butyl)benzenesulfinimidate 4af: yield: 92% (59.2mg); >95: 5dr (determined by 1 HNMR); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D20 =-45.0 (c 0.59 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28 (d, J=7.1Hz, 2H), 7.95 (d, J=8.6Hz, 2H), 7.59 (d, J=8.6Hz, 2H), 7.49 (t, J=7.3Hz, 1H), 7.42 (t, J=7.5Hz, 2H), 4.80-4.73 (m, 1H), 2.21-2.14 (m, 1 H), 1.99-1.93 (m, 1H), 1.86-1.42 (m, 10H), 1.36 (s, 9H), 1.34-0.93 (m, 19H), 0.90 (d, J=6.5Hz, 3H), 0.87 (d, J=2.7Hz, 3H), 0.86 (d, J=2.7Hz, 3H), 0.79 (s, 3H), 0.64 (s, 3H); 13 C NMR (151MHz, CDCl3) δ178.7, 156.4, 136.3, 134.9, 131.7, 129.6, 128.0, 127.5, 126.5, 82.3, 56.5, 56.4, 54.3, 45.0, 42.7, 40.1, 39.6, 37. 1, 36.3, 35.9, 35.6, 35.5, 35.3, 32.0, 31.3, 30.0, 28.7, 28.4, 28.1, 24.3, 23.9, 23.0, 22.7, 21.4, 18.8, 12.4, 12.2; HRMS (ESI) m / z: [M+Na] + calculated for C 42 H 61 NNaO2S: 666.4321, found: 666.4313.

[0254] Example 33: Synthesis and Characterization of Compound 4ag

[0255]

[0256] The same method as in Example 1 was used to isolate the product 4ag with a yield of 83% and ee of 86%.

[0257] The structure of compound 4ag is as follows:

[0258]

[0259] Characterization data of compound 4ag:

[0260] isobutyl(S)-N-bennzoyl-4-fluorobenzenesulfinimidate 4ag:yield:83%(26.5mg);flash column chromatography eluent,petroleum ether / ethyl acetate=10:1;colorless oil;[α] D 20 =-197.0(c 0.27CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.30-8.25(m,2H),8.09-8.05(m,2H),7.54-7.49(m,1H),7.44(t,J=7.6Hz,2H),7.30(dd,J=12.6,4.4Hz,2H),4.06-4.01(m,1H),3.69-3.64(m,1H),1.96-1.88(m,1H),0.91-0.84(m,6H); 13 CNMR(151MHz,CDCl3)δ178.5,165.5(d,J=255.3Hz),135.9,132.7(d,J=2.4Hz),132.0,130.5(d,J=9.1Hz),129.6,128.2,116.9(d,J=22.1Hz),74.2,28.9,19.1; 19 F NMR(565MHz,CDCl3)δ-105.46;HRMS(ESI)m / z:[M+H] + calculated for C 17 H 19 FNO2S:320.115,found:320.1119;Enantiomeric excess:86%,determined by HPLC(Daicel ChiralpakIF,isopropanol / hexane=20 / 80,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =6.53min(major),t R =7.73min(minor).

[0261] Example 34: Synthesis and Characterization of Compound 4ah

[0262]

[0263] The same method as in Example 1 was used to isolate the product 4ah with a yield of 73% and ee of 92%.

[0264] The structure of compound 4ah is as follows:

[0265]

[0266] Characterization data of compound 4ah:

[0267] isobutyl(R)-N-benzoyl-4-chlorobenzenesulfinimidate 4ah: yield: 73% (24.6mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-210.5 (c 0.25 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.27 (dd, J=8.1, 0.9Hz, 2H), 7.99 (d, J=8.6Hz, 2H), 7.58 (d, J=8.6Hz, 2H), 7.52 (t, J=7.3Hz, 1H), 7 .44 (t, J=7.6Hz, 2H), 4.04 (dd, J=9.6, 6.5Hz, 1H), 3.66 (dd, J=9.6, 6.6Hz, 1H), 2.00-1.86 (m, 1H), 0.88 (t, J=6.4Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.5, 139.4, 135.8, 135.5, 132.0, 129.8, 129.6, 129.3, 128.1, 74.3, 28.9, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 17 H 19 ClNO2S: 336.0820, found: 336.0822; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.85min(major), t R =8.04min(minor).

[0268] Example 35: Synthesis and Characterization of Compound 4ai

[0269]

[0270] The same method as in Example 1 was used to isolate the product 4ai with a yield of 88% and ee of 95%.

[0271] The structure of compound 4ai is as follows:

[0272]

[0273] Characterization data of compound 4ai:

[0274] isobutyl(R)-N-benzoyl-4-bromobenzenesulfinimidate 4ai: yield: 88% (33.5mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-185.5 (c 0.23CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.27 (d, J=8.1Hz, 2H), 7.94-7.87 (m, 2H), 7.77-7.72 (m, 2H), 7.56-7.49 (m, 1H), 7.44 (t, J=7.6Hz, 2H), 4.07-4.01 (m, 1H), 3.66 (dd, J=9.5, 6.7Hz, 1H), 1.98-1.88 (m, 1H), 0.88 (t, J=6.2Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.5, 136.1, 135.8, 132.8, 132.1, 129.6, 129.5, 128.2, 127.8, 74.4, 28.9, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 17 H 19BrNO2S: 380.0314, found: 380.0324; Enantiomeric excess: 95%, determined by HPLC (Daicel ChiralpakIF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.29min(major), t R =8.57min(minor).

[0275] Example 36: Synthesis and Characterization of Compound 4aj

[0276]

[0277] The same method as in Example 1 was used to isolate the product 4aj with a yield of 71% and ee of 95%.

[0278] The structure of compound 4aj is as follows:

[0279]

[0280] Characterization data of compound 4aj:

[0281] isobutyl(R)-N-benzoyl-4-(trifluoromethyl)benzenesulfinimidate 4aj: yield: 71% (26.4mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-195.1 (c 0.23CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28 (d, J=7.5Hz, 2H), 8.18 (d, J=8.2Hz, 2H), 7.87 (d, J=8.2Hz, 2H), 7.53 (dd, J=10.7, 4.0Hz, 1H) , 7.45 (t, J=7.5Hz, 2H), 4.10 (dd, J=9.5, 6.6Hz, 1H), 3.73 (dd, J=9.5, 6.6Hz, 1H), 2.01-1.92 (m, 1H), 0.92-0.89 (m, 6H); 13C NMR (151MHz, CDCl3) δ178.6, 141.2, 135.6, 134.6 (q, J=32.7Hz), 132.2, 129.6, 128.5, 128.2, 126.5 (q, J=3.6Hz), 123.5 (q, J=272.7Hz), 77.3, 77.1, 76.8, 75.0, 29.0, 19.0; 19 F NMR (565MHz, CDCl3) δ-63.05; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 18 F3NNaO2S: 392.0903, found: 392.0904; Enantiomericexcess: 95%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =5.71min(major), t R =6.08min(minor).

[0282] Example 37: Synthesis and Characterization of Compound 4ak

[0283]

[0284] The same method as in Example 1 was used to isolate the product 4ak with a yield of 44% and ee of 87%.

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

[0286]

[0287] Characterization data of compound 4ak:

[0288] isobutyl(R)-N-benzoyl-4-cyanobenzenesulfinimidate 4ak: yield: 44% (14.2mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-114.1 (c 0.14CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.25 (d, J=7.1Hz, 2H), 8.17 (d, J=8.2Hz, 2H), 7.89 (d, J=8.1Hz, 2H), 7.53 (t, J=7.3H z, 1H), 7.45 (t, J=7.5Hz, 2H), 4.15-4.06 (m, 1H), 3.82-3.72 (m, 1H), 2.02-1.93 (m, 1H), 0.94-0.87 (m, 6H); 13 C NMR (151MHz, CDCl3) δ178.6, 142.2, 135.4, 133.1, 132.3, 129.6, 128.7, 128.3, 117.6, 116.5, 75.4, 29.0, 19.0; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 18 N2NaO2S: 349.0987, found: 349.0988; Enantiomeric excess: 87%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.59min(major), t R =11.74min(minor).

[0289] Example 38: Synthesis and Characterization of Compound 4a1

[0290]

[0291] The same method as in Example 1 was used to isolate the product 4al with a yield of 66% and ee of 84%.

[0292] The structure of compound 4al is as follows:

[0293]

[0294] Characterization data of compound 4al:

[0295] isobutyl(R)-N-benzoyl-4-nitrobenzenesulfinimidate 4al: yield: 66% (22.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-137.7 (c 0.23CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.44 (d, J=8.6Hz, 2H), 8.36-8.19 (m, 4H), 7.54 (t, J=7.3Hz, 1H), 7.45 (t, J=7.5Hz, 2H), 4.12 ( dd, J=9.5, 6.6Hz, 1H), 3.79 (dd, J=9.4, 6.7Hz, 1H), 2.05-1.94 (m, 1H), 0.92 (d, J=5.3Hz, 3H), 0.91 (d, J=6.1Hz, 3H); 13 C NMR (151MHz, CDCl3) δ178.6, 150.4, 143.8, 135.3, 132.4, 129.6, 129.2, 128.3, 124.6, 75.5, 29.0, 19.0; HRMS (ESI) m / z: [M+Na] + calculated for C 17 H18N2NaO4S: 369.0885, found: 369.0885; Enantiomeric excess: 84%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.38min(major), t R =13.03min(minor).

[0296] Example 39: Synthesis and Characterization of Compound 4am

[0297]

[0298] The same method as in Example 1 was used to isolate the product 4am with a yield of 62% and ee of 85%.

[0299] The structure of compound 4am is as follows:

[0300]

[0301] Characterization data of compound 4am:

[0302] methyl (R)-4-(N-benzoyl-isobutoxysulfinimidoyl)benzoate 4am: yield: 62% (22.2 mg); flash column chromatography eluent, petroleum ether / ethyl acetate = 10:1; colorless oil; [α] D 20 = -107.7 (c 0.22 CH2Cl2); 1 1H NMR (600 MHz, CDCl3) δ 8.31 - 8.23 (m, 4H), 8.12 (d, J = 8.5 Hz, 2H), 7.52 (t, J = 6.7 Hz, 1H), 7.44 (t, J = 7.5 Hz, 2H), 4.07 (dd, J = 9.6, 6.5 Hz, 1H), 3.98 (s, 3H), 3.70 (dd, J = 9.5, 6.6 Hz, 1H), 1.99 - 1.90 (m, 1H), 0.89 (t, J = 6.5 Hz, 6H); 13 13C NMR (151 MHz, CDCl3) δ 178.6, 165.9, 141.5, 135.7, 134.1, 132.1, 130.6, 129.6, 128.2, 128.0, 74.7, 52.8, 29.0, 19.0; HRMS (ESI) m / z: [M+Na] + calculated for C 19 H 21 NNaO4S: 382.1089, found: 382.1090; Enantiomeric excess: 85%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane = 20 / 80, flow rate = 1.0 mL / min, T = 30 °C, λ = 254 nm): t R = 8.69 min (major), t R = 10.64 min (minor).

[0303] Example 40: Synthesis and Characterization of Compound 4an

[0304]

[0305] The same method as in Example 1 was used to isolate the product 4an with a yield of 97% and ee of 84%.

[0306] The structure of compound 4an is as follows:

[0307]

[0308] Characterization data of compound 4an:

[0309] isobutyl(R)-N-benzoylbenzenesulfinimidate 4an: yield: 97% (29.1mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-237.3 (c 0.24CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.32-8.28 (m, 2H), 8.05 (dd, J=8.0, 1.3Hz, 2H), 7.65-7.59 (m, 3H), 7.51 (t, J=7.3Hz, 1H), 7.44 (dd , J=11.4, 4.0Hz, 2H), 4.05 (dd, J=9.6, 6.6Hz, 1H), 3.66 (dd, J=9.6, 6.7Hz, 1H), 1.98-1.88 (m, 1H), 0.88 (t, J=7.0Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.5, 137.0, 136.1, 132.8, 131.9, 129.6, 129.5, 128.1, 127.9, 74.1, 28.9, 19.1; HRMS (ESI) m / z: [M+Na] + calculated for C 17 H 19 NNaO2S: 324.1029, found: 3324.1034; Enantiomeric excess: 84%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.15min(major), t R =12.23min(minor).

[0310] Example 41: Synthesis and Characterization of Compound 4ao

[0311]

[0312] The same method as in Example 1 was used to isolate the product 4ao with a yield of 97% and ee of 86%.

[0313] The structure of compound 4ao is as follows:

[0314]

[0315] Characterization data of compound 4ao:

[0316] isobutyl(R)-N-benzoyl-4-methylbenzenesulfinimidate 4ao: yield: 97% (29.1mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-189.3 (c 0.20CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.7Hz, 2H), 7.93 (d, J=7.2Hz, 2H), 7.50 (t, J=6.9Hz, 1H), 7.43 (t, J=7.2Hz, 2H), 7.39 ( d, J=7.6Hz, 2H), 4.02 (dd, J=8.0, 7.2Hz, 1H), 3.70-3.58 (m, 1H), 2.46 (s, 3H), 1.97-1.86 (m, 1H), 0.87 (t, J=6.4Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.5, 143.7, 136.2, 133.8, 131.8, 130.2, 129.6, 128.1, 127.9, 73.8, 28.9, 21.7, 19.1; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 21NNaNO2S: 338.1185, found: 338.1186; Enantiomeric excess: 86%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.40min(major), t R =9.30min(minor).

[0317] Example 42: Synthesis and Characterization of Compound 4ap

[0318]

[0319] The same method as in Example 1 was used to isolate the product 4ap with a yield of 81% and ee of 78%.

[0320] The structure of compound 4ap is as follows:

[0321]

[0322] Characterization data of compound 4ap:

[0323] isobutyl(R)-N-benzoyl-4-isopropylbenzenesulfinimidate 4ap: yield: 81% (27.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-114.1 (c 0.18CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.7Hz, 2H), 7.96 (d, J=8.2Hz, 2H), 7.50 (t, J=7.3Hz, 1H), 7.44 (dd, J=14.4, 7.7Hz, 4H), 4.05 (dd, J =9.6, 6.6Hz, 1H), 3.68 (dd, J=9.5, 6.7Hz, 1H), 3.09-2.93 (m, 1H), 2.01-1.87 (m, 1H), 1.30 (d, J=6.9Hz, 6H), 0.88 (t, J=6.8Hz, 6H); 13C NMR (151MHz, CDCl3) δ178.5, 154.4, 136.1, 134.0, 131.8, 129.6, 128.1, 128.0, 127.7, 74.1, 34.3, 28.9, 23.86, 23.85, 19.1;; HRMS (ESI) m / z: [M+Na] + calculated for C 20 H 25 NNaO2S: 366.1498, found: 36.1504; Enantiomeric excess: 78%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.53min(major), t R =7.43min(minor).

[0324] Example 43: Synthesis and Characterization of Compound 4aq

[0325]

[0326] The same method as in Example 1 was used to isolate the product 4aq with a yield of 96% and ee of 81%.

[0327] The structure of compound 4aq is as follows:

[0328]

[0329] Characterization data of compound 4aq:

[0330] isobutyl(R)-N-benzoyl-4-methoxybenzenesulfinimidate 4aq: yield: 96% (31.9mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-175.2 (c 0.28 CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.33-8.23 (m, 2H), 8.00 (d, J=8.9Hz, 2H), 7.53-7.48 (m, 1H), 7.43 (t, J=7.5Hz, 2H), 7.09 (dd, J=9.4, 2.5 Hz, 2H), 4.00 (dd, J=9.6, 6.6Hz, 1H), 3.90 (s, 3H), 3.61 (dd, J=9.6, 6.7Hz, 1H), 1.93-1.86 (m, 1H), 0.86 (dd, J=8.1, 6.8Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.3, 163.3, 136.3, 131.8, 129.9, 129.6, 128.1, 128.0, 114.9, 73.5, 55.8, 28.9, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 18 H 22 NO3S: 332.1315, found: 332.1223; Enantiomeric excess: 81%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =7.40min(major), t R =9.76min(minor).

[0331] Example 44: Synthesis and Characterization of Compound 4ar

[0332]

[0333] The same method as in Example 1 was used to isolate the product 4ar with a yield of 74% and an ee of 84%.

[0334] The structure of compound 4ar is as follows:

[0335]

[0336] Characterization data of compound 4ar:

[0337] isobutyl(R)-N-benzoyl-3-rt-uorobenzenesulfinimidate 4ar:yield:74%(23.7mg);flash column chromatography eluent,petroleum ether / ethyl acetate=10:1;colorless oil;[α] D 20 =-201.4(c 0.19CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.28(d,J=7.8Hz,2H),7.85(d,J=8.4Hz,1H),7.78(d,J=7.8Hz,1H),7.59(td,J=8.0,5.5Hz,1H),7.53(t,J=7.1Hz,1H),7.45(t,J=7.6Hz,2H),7.33(td,J=8.2,2.5Hz,1H),4.06(dd,J=9.4,6.6Hz,1H),3.68(dd,J=9.5,6.7Hz,1H),2.03-1.89(m,1H),0.90(t,J=6.1Hz,6H); 13 CNMR(151MHz,CDCl3)δ178.5,165.5(d,J=255.3Hz),135.9,132.7(d,J=2.4Hz),132.0,130.5(d,J=9.1Hz),129.6,128.2,116.9(d,J=22.1Hz),74.2,28.9,19.1; 19 F NMR(565MHz,CDCl3)δ-109.13;HRMS(ESI)m / z:[M+H] + calculated for C 17 H 19 FNO2S:320.1121,found:320.1129;Enantiomeric excess:84%,determined by HPLC(Daicel ChiralpakIF,isopropanol / hexane=20 / 80,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =6.37min(major),t R =6.79min(minor).

[0338] Example 45: Synthesis and characterization of compound 4as

[0339]

[0340] The same method as in Example 1 was used to isolate the product 4as with a yield of 72% and ee of 87%.

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

[0342]

[0343] Characterization data of compound 4as:

[0344] isobutyl(R)-N-benzoyl-3-chlorobenzenesulfinimidate 4as: yield: 72% (24.2mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-154.0 (c 0.25 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.30-8.26 (m, 2H), 8.07 (d, J=1.3Hz, 1H), 7.89 (dd, J=7.8, 0.9Hz, 1H), 7.59 (dd, J=8.0, 0.9Hz, 1H), 7.56-7.51 (m , 2H), 7.45 (t, J=7.6Hz, 2H), 4.05 (dd, J=9.5, 6.6Hz, 1H), 3.68 (dd, J=9.5, 6.7Hz, 1H), 1.99-1.90 (m, 1H), 0.89 (dd, J=6.5, 4.9Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.5, 138.8, 135.70, 135.65, 133.0, 132.1, 130.7, 129.6, 128.2, 127.8, 126.2, 74.4, 28.9, 19.0HRMS (ESI) m / z: [M+H] + calculated for C 17 H 19ClNO2S: 336.0820, found: 336.0825; Enantiomeric excess: 87%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.64min(major), t R =7.13min(minor).

[0345] Example 46: Synthesis and Characterization of Compound 4at

[0346]

[0347] The same method as in Example 1 was used to isolate the product 4at with a yield of 73% and ee of 85%.

[0348] The structure of compound 4at is as follows:

[0349]

[0350] Characterization data of compound 4at:

[0351] isobutyl(R)-N-benzoyl-3-bromobenzenesulfinimidate 4at: yield: 73% (27.6mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-156.3 (c 0.34CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8-30-8.25 (m, 2H), 8.21 (t, J=1.6Hz, 1H), 7.94 (d, J=7.9Hz, 1H), 7.76 (dd, J=8.0, 0.7Hz, 1H), 7.53 (t, J=7.3H z, 1H), 7.50-7.43 (m, 3H), 4.05 (dd, J=9.6, 6.5Hz, 1H), 3.68 (dd, J=9.6, 6.7Hz, 1H), 1.99-1.91 (m, 1H), 0.90 (dd, J=6.7, 4.4Hz, 6H); 13C NMR (151MHz, CDCl3) δ178.5, 139.1, 135.9, 135.7, 132.1, 131.0, 130.7, 129.6, 128.2, 126.7, 123.5, 74.5, 28.9, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 17 H 19 BrNO2S: 380.0314, found: 380.0319; Enantiomeric excess: 85%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.84min(major), t R =7.42min(minor).

[0352] Example 47: Synthesis and Characterization of Compound 4au

[0353]

[0354] The same method as in Example 1 was used to isolate the product 4au with a yield of 71% and ee of 82%.

[0355] The structure of compound 4au is as follows:

[0356]

[0357] Characterization data of compound 4au:

[0358] isobutyl(R)-N-benzoyl-3-(trifluoromethyl)benzenesulfinimidate 4au: yield: 71% (26.1mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-174.5 (c 0.20CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.32 (s, 1H), 8.29-8.26 (m, 2H), 8.23 ​​(d, J=7.9Hz, 1H), 7.89 (d, J=7.7Hz, 1H), 7.77 (t, J=7.8Hz, 1H), 7.54 (dd, J=10.6, 4.1Hz, 1H), 7.46 (t, J=7.5Hz, 2H), 4.10 (dd, J=9.6, 6.5Hz, 1H), 3.73 (dd, J=9.5, 6.7Hz, 1H), 2.04-1.88 (m, 1H), 0.91 (dd, J=6.6, 4.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.6, 138.7, 135.6, 132.2, 131.3, 132.2 (q, J=33.2Hz), 130.2, 129. 6, 129.5 (q, J = 3.5Hz), 128.2, 125.0 (q, J = 3.8Hz), 123.4 (q, J = 272.4Hz), 75.0, 29.0, 19.0; 19 F NMR (565MHz, CDCl3) δ-62.81; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 18 F3NNaO2S: 392.0903, found: 392.0904; Enantiomeric excess: 82%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.05min(major), t R =10.72min(minor).

[0359] Example 48: Synthesis and Characterization of Compound 4av

[0360]

[0361] The same method as in Example 1 was used to isolate the product 4av with a yield of 90% and ee of 79%.

[0362] The structure of compound 4av is as follows:

[0363]

[0364] Characterization data of compound 4av:

[0365] isobutyl(R)-N-benzoyl-3-methylbenzenesulfinimidate 4av: yield: 90% (28.5mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-35.5 (c 0.06CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (d, J=7.4Hz, 2H), 7.84 (s, 2H), 7.53-7.47 (m, 2H), 7.46-7.41 (m, 3H), 4.04 (dd , J=9.6, 6.6Hz, 1H), 3.66 (dd, J=9.5, 6.7Hz, 1H), 2.49 (s, 3H), 1.98-1.89 (m, 1H), 0.88 (t, J=6.4Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.6, 139.7, 136.7, 136.1, 133.7, 131.8, 129.6, 129.4, 128.1, 128.1, 125.1, 74.1, 28.9, 21.7, 19.1; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 22 NO2S: 316.1366, found: 316.1363; Enantiomeric excess: 79%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.63min(major), t R =7.44min(minor).

[0366] Example 49: Synthesis and Characterization of Compound 4aw

[0367]

[0368] The same method as in Example 1 was used to finally separate the product 4aw with a yield of 76% and ee of 70%.

[0369] The structure of compound 4aw is as follows:

[0370]

[0371] Characterization data of compound 4aw:

[0372] isobutyl(R)-N-benzoyl-2-methylbenzenesulfinimidate 4aw: yield: 76% (24.0mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-122.2 (c 0.19 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.50 (d, J=7.9Hz, 1H), 8.29 (d, J=8.0Hz, 2H), 7.53-7.49 (m, 2H), 7.48-7.42 (m, 3H), 7.34 (d, J=7.4Hz, 1H), 3.98 (dd, J=9.4, 6.5Hz, 1H), 3.59 (dd, J=9.4, 6.8Hz, 1H), 2.64 (s, 3H), 1.92-1.82 (m, 1H), 0.84 (dd, J=12.0, 6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.3, 138.6, 136.3, 134.8, 133.0, 131.8, 131.7, 129. 6, 128.1, 127.4, 126.9, 73.7, 28.8, 19.2, 19.03, 19.0; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 22 NO2S: 316.1366, found: 316.1364; Enantiomeric excess: 70%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.54min(major), t R =7.13min(minor).

[0373] Example 50: Synthesis and Characterization of Compound 4ax

[0374]

[0375] The same method as in Example 1 was used to isolate the product 4ax with a yield of 84% and ee of 89%.

[0376] The structure of compound 4ax is as follows:

[0377]

[0378] Characterization data of compound 4ax:

[0379] isobutyl(R)-N-benzoyl-3, 4-dirt-uorobenzenesulfinimidate 4ax: yield: 84% (28.2mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-210.0 (c 0.22 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.28-8.23 (m, 2H), 8.02-7.96 (m, 1H), 7.81-7.75 (m, 1H), 7.55-7.51 (m, 1H), 7.47-7.3 9 (m, 3H), 4.05 (dd, J=9.5, 6.6Hz, 1H), 3.67 (dd, J=9.5, 6.7Hz, 1H), 1.98-1.90 (m, 1H), 0.89 (t, J=6.0Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.4, 153.3 (dd, J=257.0, 12.7Hz), 150.8 (dd, J=254.4, 13.2Hz), 135.6, 133.8-133.7 (m ), 132.2, 129.6, 128.2, 125.0 (dd, J=7.3, 3.8Hz), 118.6 (d, J=18.1Hz), 117.6 (d, J=20.3Hz), 74.5, 28.9, 19.0; 19 F NMR (565MHz, CDCl3) δ-129.58 (d, J=20.2Hz), -133.04 (d, J=20.2Hz); HRMS (ESI) m / z: [M+Na] + calculated for C 17 H 17F2NNaO2S: 360.0840, found: 360.0846; Enantiomeric excess: 89%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =11.88min(major), t R =13.23min(minor).

[0380] Example 51: Synthesis and characterization of compound 4ay

[0381]

[0382] The same method as in Example 1 was used to finally separate the product 4ay with a yield of 85% and ee of 87%.

[0383] The structure of compound 4ay is as follows:

[0384]

[0385] Characterization data of compound 4ay:

[0386] isobutyl(R)-N-benzoylthiophene-2-sulfinimidate 4ay: yield: 85% (26.1mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-51.5 (c 0.18CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.26 (dd, J=8.2, 1.3Hz, 2H), 7.76 (dd, J=5.0, 1.2Hz, 1H), 7.68 (dd, J=3.8, 1.2Hz, 1H), 7.54-7.49 (m, 1H), 7.44 (t ; 13C NMR (151MHz, CCDCl3) δ178.1, 135.4, 133.6, 132.5, 132.0, 129.6, 128.7, 128.1, 72.1, 28.7, 19.1; HRMS (ESI) m / z: [M+Na] + calculated for C 15 H 17 NNaO2S2: 330.0593, found: 330.0597; Enantiomericexcess: 87%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.82min(major), t R =8.50min(minor)

[0387] Example 52: Synthesis and Characterization of Compound 4az

[0388]

[0389] The same method as in Example 1 was used to isolate the product 4az with a yield of 95% and ee of 81%.

[0390] The structure of compound 4az is as follows:

[0391]

[0392] Characterization data of compound 4az:

[0393] isobutyl(R)-N-benzoylcyclohexan-sulfinimidate 4az: yield: 95% (29.2mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-198.8 (c 0.27CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.18 (d, J=7.4Hz, 2H), 7.47 (t, J=7.3Hz, 1H), 7.39 (t, J=7 .5Hz, 2H), 4.13-4.05(m, 2H), 3.14(t, J=11.4Hz, 1H), 2.21(s, 2H), 2.02-1.96(m , 1H), 1.94-1.87 (m, 2H), 1.73 (d, J=13.4Hz, 1H), 1.58 (dt, J=16.2, 12.0Hz, 2H) , 1.40 (dd, J=25.1, 12.4Hz, 2H), 1.34-1.28 (m, 1H), 0.94 (dd, J=6.6, 3.5Hz, 6H); 13 C NMR (151MHz, CDCl3) δ179.3, 136.3, 131.6, 129.5, 128.0, 78.8, 59.3, 29.4, 26.4, 25.6, 25.4, 19.1; HRMS (ESI) m / z: [M+Na] + calculated for C 17 H 25 NNaO2S2: 330.1498, found: 330.1497; Enantiomeric excess: 81%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =13.23(minor)min,t R =14.31min(major).

[0394] Example 53: Synthesis and Characterization of Compound 4ba

[0395]

[0396] The same method as in Example 1 was used to finally separate the product 4ba with a yield of 90% and ee of 70%.

[0397] The structure of compound 4ba is as follows:

[0398]

[0399] Characterization data of compound 4ba:

[0400] isobutyl(R)-N-benzoylpentasulfinimidate 4ba: yield: 90% (25.3mg); flashcolumn chromatography eluent, petroleum ether / ethyl acetate=10:1; colorlessoil; [α] D 20 =-160.6 (c 0.23CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.21-8.13 (m, 2H), 7.47 (t, J=7.3Hz, 1H), 7.40 (t, J=7.6Hz, 2H), 4.09 (d, J=6.6Hz, 2H), 3.24-3.18 (m, 1H), 3.16-3.10 (m, 1H), 2.02-1.93 (m, 1H), 1.84-1.78 (m, 2H), 1.56-1.49 (m, 2H), 0.99 (t, J=7.4Hz, 3H), 0.94 (dd, J=6.7, 3.0Hz, 6H); 13 C NMR (151MHz, CDCl3) δ179.1, 135.9, 131.7, 129.5, 128.1, 78.6, 50.6, 29.3, 25.2, 21.9, 19.00, 18.97, 13.8; HRMS (ESI) m / z: [M+Na] + calculated for C 15 H 23 NNaO2S: 304.1342, found: 304.1343; Enantiomeric excess: 70%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =11.76(minor)min,t R =14.30min(major).

[0401] Example 54: Synthesis and Characterization of Compound 4bb

[0402]

[0403] The same method as in Example 1 was used to isolate the product 4bb with a yield of 95% and ee of 69%.

[0404] The structure of compound 4bb is as follows:

[0405]

[0406] Characterization data of compound 4bb:

[0407] isobutyl (R)-N-benzoyl-2-phenylacesulfinimidate 4bb: yield: 95% (3o.o mg); flash column chromatography eluent, petroleum ether / ethyl acetate = 10:1; colorless oil; [α] D 20 = -198.3 (c 0.28 CH2Cl2); 1 1H NMR (600 MHz, CDCl3) δ 8.16 (d, J = 7·1 Hz, 2H), 7.58 - 7.33 (m, 8H), 4.49 (dd, J = 13.3, 1.8 Hz, 1H), 4.42 - 4.33 (m, 1H), 4.09 - 4.02 (m, 1H), 4.00 - 3.92 (m, 1H), 1.91 - 1.80 (m, 1H), 0.82 (d, J = 6.0 Hz, 6H); 13 13C NMR (151 MHz, CDCl3) δ 179.0, 135.8, 131.8, 131.0, 129.5, 129.09, 129.06, 129.05, 128.1, 79.1, 57.3, 29.2, 18.9; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 21 NNaO2S: 338.1185, found: 338.1185; Enantiomeric excess: 69%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane = 30 / 70, flow rate = 1.0 mL / min, T = 30 °C, λ = 254 nm): t R = 6.46 (minor) min, t R = 11.35 min (major).

[0408] Example 55: Synthesis and Characterization of Compound 4bc

[0409]

[0410] The same method as in Example 1 was used to isolate the product 4bc with a yield of 88% and ee of 79%.

[0411] The structure of compound 4bc is as follows:

[0412]

[0413] Characterization data of compound 4bc:

[0414] isobutyl(R)-N-benzoyl-2-(m-tolyl)acesulfinimidate 4ay: yield: 88% (29.1mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-79.5 (c 0.14CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.16 (dd, J=5.1, 3.3Hz, 2H), 7.48 (ddd, J=8.6, 2.5, 1.2Hz, 1H), 7.40 (dd, J=10.5, 4.6Hz, 2H), 7.30-7.25 (m, 2H), 7.23 (d, J=7.6Hz, 1H), 7.18 (d, J=7. 5Hz, 1H), 4.46 (d, J=13.2Hz, 1H), 4.35 (d, J=13.2Hz, 1H), 4.06 (dd, J=9.8, 6.6Hz, 1H) , 3.96 (dd, J=9.8, 6.5Hz, 1H), 2.37 (s, 3H), 1.90-1.81 (m, 1H), 0.84 (d, J=6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.9, 138.8, 135.8, 131.8, 129.8, 129.5, 128.9, 128.8, 128.1, 128.0, 79.1, 57.2, 29.3, 21.4, 18.9; HRMS (ESI) m / z: [M+Na] + calculated for C 19 H 23NNaO2S: 352.1342, found: 352.1347; Enantiomeric excess: 79%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.05(minor)min,t R =11.70min(major).

[0415] Example 56: Synthesis and Characterization of Compound 4bd

[0416]

[0417] The same method as in Example 1 was used to isolate the product 4bd with a yield of 86% and ee of 92%.

[0418] The structure of compound 4bd is as follows:

[0419]

[0420] Characterization data of compound 4bd:

[0421] isobutyl(R)-4-(tert-butyl)-N-(4-fluorobenzoyl)benzenesulfinimidate4bd: yield: 86% (32.4mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-152.5 (c 0.12CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.29 (dd, J=8.2, 5.9Hz, 2H), 7.94 (d, J=8.4Hz, 2H), 7.61 (d, J=8.4Hz, 2H), 7.08 (t, J=8.6Hz, 2 H), 4.05 (dd, J=9.5, 6.6Hz, 1H), 3.70 (dd, J=9.5, 6.7Hz, 1H), 1.99-1.89 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.5Hz, 6H); 13C NMR (151MHz, CDCl3) δ177.4, 165.3 (d, J = 251.6Hz), 156.8, 133.6, 132.5 (d, J = 2.1Hz), 132.0 (d, J=8.9Hz), 127.7, 126.6, 115.0 (d, J=21.6Hz), 74.4, 35.3, 31.3, 29.0, 19.1; 19 F NMR (565MHz, CDCl3) δ-108.57; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 27 FNO2S: 376.1741, found: 376.1746; Enantiomericexcess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.25min(major), t R =8.02min(minor).

[0422] Example 57: Synthesis and Characterization of Compound 4be

[0423]

[0424] The same method as in Example 1 was used to isolate the product 4be with a yield of 78% and ee of 92%.

[0425] The structure of compound 4be is as follows:

[0426]

[0427] Characterization data of compound 4be:

[0428] isobutyl(R)-4-(tert-butyl)-N-(4-chlorobenzoyl)benzenesulfinimidate4be: yield: 78% (30.5mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-168.4 (c 0.04CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.21 (d, J=8.5Hz, 2H), 7.94 (d, J=8.5Hz, 2H), 7.61 (d, J=8.5Hz, 2H), 7.39 (d, J=8.5Hz, 2H), 4.04 (dd, J=9.6, 6.6Hz, 1H), 3.69 (dd, J=9.6, 6.6Hz, 1H), 1.98-1.89 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.5Hz, 6H); 13 C NMR (126MHz, CDCl3) δ177.5, 156.8, 138.0, 134.7, 133.5, 131.0, 128.3, 127.6, 126.6, 74.4, 35.3, 31.2, 28.9, 19.1, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 27 ClNO2S: 392.1446, found: 392.1447; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =13.03min(major), t R =14.04min(minor).

[0429] Example 58: Synthesis and Characterization of Compound 4bf

[0430]

[0431] The same method as in Example 1 was used to isolate the product 4bf with a yield of 75% and ee of 92%.

[0432] The structure of compound 4bf is as follows:

[0433]

[0434] Characterization data of compound 4bf:

[0435] isobutyl(R)-N-(4-bromobenzoyl)-4-(tert-butyl)benzenesulfinimidate4bf: yield: 75% (32.6mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-88.9 (c 0.06CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.14 (d, J=8.5Hz, 2H), 7.94 (d, J=8.6Hz, 2H), 7.61 (d, J=8.6Hz, 2H), 7.55 (d, J=8.5Hz, 2H), 4.04 (dd, J=9.6, 6.6Hz, 1H), 3.69 (dd, J=9.6, 6.6Hz, 1H), 1.98-1.88 (m, 1H), 1.37 (s, 9H), 0.88 (t, J=6.5Hz, 6H); 13 C NMR (151MHz, CDCl3) δ177.6, 156.9, 135.1, 133.5, 131.3, 131.2, 127.7, 126.7, 126.6, 74.4, 35.3, 31.2, 28.9, 19.1, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 27 BrNO2S: 436.0940, found: 436.0945; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =6.24min(minor), t R =6.94min(major).

[0436] Example 59: Synthesis and Characterization of Compound 4bg

[0437]

[0438] The same method as in Example 1 was used to isolate the product 4bg with a yield of 77% and ee of 91%.

[0439] The structure of compound 4bg is as follows:

[0440]

[0441] Characterization data of compound 4bg:

[0442] isobutyl(R)-4-(tert-butyl)-N-(4-(trifluoromethyl)benzenesulfinimidate4bg: yield: 77% (32.9mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-186.2 (c 0.05CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.38 (d, J=8.1Hz, 2H), 7.95 (d, J=8.5Hz, 2H), 7.68 (d, J=8.2Hz, 2H), 7.63 (d, J=8.5Hz, 2H), 4.05 (dd, J=9.6, 6.6Hz, 1H), 3.71 (dd, J=9.6, 6.6Hz, 1H), 1.98-1.90 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.5Hz, 6H); 13 C NMR (151MHz, CDCl3) δ177.1, 157.0, 139.5133.2 (q, J=32.3Hz), 129.9, 127.7, 126.7 , δ125.1 (q, J=3.8Hz), 124.2 (q, J=272.3Hz).74.6, 35.4, 31.2, 28.9, 19.03, 19.02; 19 F NMR (565MHz, CDCl3) δ-62.75; HRMS (ESI) m / z: [M+H] + calculated for C 22 H 27 F3NO2S: 426.1709, found: 426.1704; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =8.29min(major), tR =9.17min(minor).

[0443] Example 60: Synthesis and Characterization of Compound 4bh

[0444]

[0445] The same method as in Example 1 was used to isolate the product 4bh with a yield of 99% and ee of 91%.

[0446] The structure of compound 4bh is as follows:

[0447]

[0448] Characterization data of compound 4bh:

[0449] isobutyl(R)-4-(tert-butyl)-N-(4-cyanobenzoyl)benzenesulfinimidate4bh: yield: 99% (38.0mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-144.4 (c 0.24 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.35 (d, J=8.3Hz, 2H), 7.94 (d, J=8.5Hz, 2H), 7.72 (d, J=8.3Hz, 2H), 7.63 (d, J=8.5Hz, 2H), 4.04 (dd, J=9.5, 6.6Hz, 1H), 3.70 (dd, J=9.5, 6.6Hz, 1H), 2.00-1.89 (m, 1H), 1.37 (s, 9H), 0.88 (t, J=6.5Hz, 6H); 13 C NMR (151MHz, CDCl3) δ176.5, 157.2, 140.2, 133.1, 132.0, 130.0, 127.6, 126. 8, 118.8, 115.0, 74.8, 35.4, 31.2, 28.9, 19.02, 19.00; HRMS (ESI) m / z: [M+H] + calculated for C 22 H 27N2NO2S: 383.1788, found: 383.1786; Enantiomericexcess: 91%, determined by HPLC (Daicel Chiralpak IC, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =11.16min(major), t R =12.19min(minor).

[0450] Example 61: Synthesis and Characterization of Compound 4bi

[0451]

[0452] The same method as in Example 1 was used to isolate the product 4bi with a yield of 85% and ee of 90%.

[0453] The structure of compound 4bi is as follows:

[0454]

[0455] Characterization data of compound 4bi:

[0456] isobutyl(R)-4-(tert-butyl)-N-(4-nitrobenzoyl)benzenesulfinimidate4bi: yield: 85% (34.1mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-97.1 (c 0.06CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.41 (d, J=8.9Hz, 2H), 8.25 (d, J=8.9Hz, 2H), 7.95 (d, J=8.6Hz, 2H), 7.64 (d, J=8.6Hz, 2H), 4.05 (dd, J=9.6, 6.5Hz, 1H), 3.72 (dd, J=9.6, 6.6Hz, 1H), 1.99-1.91 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.5Hz, 6H); 13C NMR (151MHz, CDCl3) δ176.3, 157.2, 149.9, 141.8, 133.0, 130.5, 127.7, 126.8, 123.3, 74.9, 35.4, 31.2, 28.9, 19.01, 18.99; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 27 N2O4S: 403.1686, found: 403.1690; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =11.90min(major), t R =15.59min(minor).

[0457] Example 62: Synthesis and Characterization of Compound 4bj

[0458]

[0459] The same method as in Example 1 was used to isolate the product 4bj with a yield of 87% and ee of 91%.

[0460] The structure of compound 4bj is as follows:

[0461]

[0462] Characterization data of compound 4bj:

[0463] methyl(R)-4-(((4-(tert-butyl)benzene)(isobutoxy)-λ 4 -sulfaneylidene)car bamoyl)benzoate 4bj: yield: 87% (36.1mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-227.2(c0.31CH2Cl2); 1H NMR (600MHz, CDCl3) δ8.32 (d, J=8.1Hz, 2H), 8.09 (d, J=8.1Hz, 2H), 7.96 (d, J=8.4Hz, 2H), 7.63 (d, J=8.4Hz, 2H), 4.06 ( dd, J=9.4, 6.7Hz, 1H), 3.94 (s, 3H), 3.71 (dd, J=9.4, 6.7Hz, 1H), 1.98-1.91 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.5Hz, 6H); 13 C NMR (151MHz, CDCl3) δ177.6, 166.9, 156.9, 140.2, 133.4, 132.8, 129.5, 129.4 , 127.7, 126.7, 74.6, 52.4, 35.3, 31.3, 28.9, 19.1, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 23 H 30 NO4S: 416.1890, found: 416.1896; Enantiomeric excess: 91%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =13.79min(major), t R =14.59min(minor).

[0464] Example 63: Synthesis and Characterization of Compound 4bk

[0465]

[0466] The same method as in Example 1 was used to isolate the product 4bk with a yield of 83% and ee of 87%.

[0467] The structure of compound 4bk is as follows:

[0468]

[0469] Characterization data of compound 4bk:

[0470] isobutyl(R)-4-(tert-butyl)-N-(4-benzoyl-benzoyl)benzenesulfinimidate4b k:yield:83%(38.2mg);flash column chromatographyeluent,petroleum ether / ethyl acetate=10:1;colorless oil;[α] D 20 =-55.2(c0.38CH2Cl2); 1 H NMR(600MHz,CDCl3)δ8.37(d,J=8.0Hz,2H),7.96(d,J=8.3Hz,2H),7.83(d,J=8.0Hz,2H),7.81(d,J=7.7Hz,2H),7.62(d,J=8.3Hz,2H),7.59(t,J=7.4Hz,1H),7.48(t,J=7.6Hz,2H),4.06(dd,J=9.3,6.8Hz,1H),3.72(dd,J=9.3,6.9Hz,1H),1.99-1.90(m,1H),1.36(s,8H),0.89(t,J=6.8Hz,6H); 13 C NMR(151MHz,CDCl3)δ196.6,196.5,177.5,156.9,140.1,139.5,137.5,133.3,132.7,130.2,129.7,129.4,128.4,127.6,126.6,74.4,35.3,31.2,28.9,19.0,19.0;HRMS(ESI)m / z:[M+H] + calculated forC 28 H 32 NO3S:462.2103,found:462.2108;Enantiomeric excess:87%,determined by HPLC(Daicel Chiralpak AD,isopropanol / hexane=10 / 90,flow rate=1.0mL / min,T=30℃,λ=254nm):t R =15.95min(major),t R =17.96min(minor).

[0471] Example 64: Synthesis and Characterization of Compound 4b1

[0472]

[0473] The same method as in Example 1 was used to isolate the product 4bl with a yield of 70% and an ee of 96%.

[0474] The structure of compound 4b1 is as follows:

[0475]

[0476] Characterization data of compound 4bl:

[0477] isobutyl(R)-N-4-(tert-butyl)-N-(4-methylbenzoyl)benzenesulfinimidate4bl: yield: 70% (26.0mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α]D20=-146.9(c 0.24CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.18 (d, J=7.8Hz, 2H), 7.96 (d, J=8.4Hz, 2H), 7.61 (d, J=8.4Hz, 2H), 7.23 (d, J=7.7Hz, 2H), 4.05 ( dd, J=9.5, 6.6Hz, 1H), 3.69 (dd, J=9.5, 6.7Hz, 1H), 2.41 (s, 3H), 1.98-1.89 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.4Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.6, 156.6, 142.2, 133.9, 133.5, 129.7, 128.8, 127.7, 126.6, 74.2, 35.3, 31.3, 29.0, 21.7, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 22 H 30 NO2S: 372.1992, found: 372.1997; Enantiomeric excess: 96%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.17min(minor), tR =6.74min(major).

[0478] Example 65: Synthesis and Characterization of Compound 4bm

[0479]

[0480] The same method as in Example 1 was used to isolate the product 4bm with a yield of 61% and ee of 93%.

[0481] The structure of compound 4bm is as follows:

[0482]

[0483] Characterization data of compound 4bm:

[0484] isobutyl(R)-N-4-(tert-butyl)-N-(4-methoxybenzoyl)benzenesulfinimidate4bm: yield: 61% (23.7mg); flash column chromatography eluent, petroleum ether / emyl acetate=10:1; colorless oil; [α]D20=-179.2(c 0.13CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.25 (d, J=8.6Hz, 2H), 7.95 (d, J=8.4Hz, 2H), 7.60 (d, J=8.4Hz, 2H), 6.92 (d, J=8.6Hz, 2 H), 4.10-3.97 (m, 1H), 3.86 (s, 3H), 3.74-3.64 (m, 1H), 1.98-1.89 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.4Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.0, 162.6, 156.5, 133.9, 131.5, 127.6, 126.5, 126.2, 113.2, 73.9, 55.4, 53.6, 35.2, 31.2, 28.9, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 22 H 30NO3S: 388.1941, found: 388.1950; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.38min(minor), t R =7.66min(major).

[0485] Example 66: Synthesis and Characterization of Compound 4bn

[0486]

[0487] The same method as in Example 1 was used to isolate the product 4bn with a yield of 87% and ee of 92%.

[0488] The structure of compound 4bn is as follows:

[0489]

[0490] Characterization data of compound 4bn:

[0491] isobutyl(R)-4-(tert-butyl)-N-(3-rt-uorobenzoyl)benzenesulfinimidate4bn: yield: 87% (32.7mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-102.9 (c 0.02CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.06 (d, J=7.6Hz, 1H), 7.99-7.93 (m, 3H), 7.62 (d, J=8.5Hz, 2H), 7.39 (dd, J=13.6, 7.7Hz, 1H), 7.19 (t, J =8.0Hz, 1H), 4.04 (dd, J=9.1, 7.0Hz, 1H), 3.69 (dd, J=9.2, 7.0Hz, 1H), 1.99-1.89 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.7Hz, 6H); 13C NMR (151MHz, CDCl3) δ177.2 (d, J=2.3Hz), 162.7 (d, J=245.4Hz), 156.9, 138.6 (d, J=7.1Hz), 133.4, 129.6 (d, J=7.7Hz ), 127.7, 126.7, 125.2 (d, J = 3.0Hz), 118.7 (d, J = 21.5Hz), 116.4 (d, J = 22.7Hz), 74.4, 35.3, 31.2, 28.9, 19.05, 19.04; 19 F NMR (565MHz, CDCl3) δ-113.63; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 26 FNaNO2S: 398.1560, found: 398.1561; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =9.81min(major), t R =11.22min(minor).

[0492] Example 67: Synthesis and Characterization of Compound 4bo

[0493]

[0494] The same method as in Example 1 was used to isolate the product 4bo with a yield of 77% and ee of 92%.

[0495] The structure of compound 4bo is as follows:

[0496]

[0497] Characterization data of compound 4bo:

[0498] isobutyl(R)-4-(tert-butyl)-N-(3-chlorobenzoyl)benzenesulfinimidate4bo: yield: 77% (30.2mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D20 =-633.3 (c 0.02CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.26 (s, 1H), 8.15 (d, J=7.7Hz, 1H), 7.95 (d, J=8.4Hz, 2H), 7.62 (d, J=8.4Hz, 2H), 7.46 (dd, J=7.9, 0.8Hz, 1H), 7 .36 (t, J=7.8Hz, 1H), 4.04 (dd, J=9.5, 6.6Hz, 1H), 3.69 (dd, J=9.5, 6.6Hz, 1H), 2.00-1.87 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.7Hz, 6H); 13 CNMR (151MHz, CDCl3) δ177.1, 156.9, 138.1, 134.1, 133.3, 131.7, 129.7, 129.4, 1 27.7, 127.6, 126.7, 74.4, 35.3, 31.2, 28.9, 19.04, 19.03; HRMS (ESI) m / z: [M+Na] + calculated for C 18 H 26 ClNaNO2S: 414.1265found: 414.1266; Enantiomeric excess: 92%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =10.59min(major), t R =11.89min(minor).

[0499] Example 68: Synthesis and Characterization of Compound 4bp

[0500]

[0501] The same method as in Example 1 was used to isolate the product 4bp with a yield of 73% and ee of 94%.

[0502] The structure of compound 4bp is as follows:

[0503]

[0504] Characterization data of compound 4bp:

[0505] isobutyl(R)-N-(3-bromobenzoyl)-4-(tert-butyl)benzenesulfinimidate4bp: yield: 73% (31.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-153.9 (c 0.34CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.42 (s, 1H), 8.19 (d, J=7.6Hz, 1H), 7.94 (d, J=8.1Hz, 2H), 7.67-7.58 (m, 3H), 7.30 (t, J=7 .7Hz, 1H), 4.03 (t, J=8.0Hz, 1H), 3.69 (t, J=8.0Hz, 1H), 1.99-1.89 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.3Hz, 6H); 13 C NMR (151MHz, CDCl3) δ177.0, 156.9, 138.3, 134.6, 133.4, 132.6, 129.7, 128.1, 127.7, 126.7, 122.3, 74.4, 35.4, 31.3, 28.9, 19.1, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 27 BrNO2S: 436.0940, found: 436.0949; Enantiomeric excess: 94%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =7.80min(minor), t R =8.46min(major).

[0506] Example 69: Synthesis and Characterization of Compound 4bq

[0507]

[0508] The same method as in Example 1 was used to isolate the product 4bq with a yield of 98% and ee of 93%.

[0509] The structure of compound 4bq is as follows:

[0510]

[0511] Characterization data of compound 4bq:

[0512] isobutyl(R)-N-4-(tert-butyl)-N-(3-methoxybenzoyl)benzenesulfinimidate4bq: yield: 98% (37.8mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α]D20=-167.7(c 0.30CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.95 (d, J=8.6Hz, 2H), 7.91 (d, J=7.6Hz, 1H), 7.83-7.81 (m, 1H), 7.61 (d, J=8.6Hz, 2H), 7.34 (t, J=7.9Hz, 1H), 7.08- 7.03 (m, 1H), 4.05 (dd, J=9.6, 6.6Hz, 1H), 3.87 (d, 3H), 3.70 (dd, J=9.6, 6.6Hz, 1H), 1.99-1.90 (m, 1H), 1.37 (s, 9H), 0.89 (t, J=6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ178.4, 159.5, 156.7, 137.7, 133.7, 129.1, 127.7, 126.6, 122.2, 118.3, 114.0, 74.3, 55.5, 35.3, 31.3, 29.0, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 22 H 30 NO3S: 388.1941, found: 388.1940; Enantiomeric excess: 93%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =4.92min(major), t R =5.40min(minor).

[0513] Example 70: Synthesis and Characterization of Compound 4br

[0514]

[0515] The same method as in Example 1 was used to finally separate the product 4br with a yield of 98% and ee of 88%.

[0516] The structure of compound 4br is as follows:

[0517]

[0518] Characterization data of compound 4br:

[0519] isobutyl(R)-4-(tert-butyl)-N-(3,5-dichlorobenzoyl)benzenesulfinimidate 4br: yield: 98% (41.7mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-128.3(c0.43CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.17-8.10(m, 2H), 7.96-7.91(m, 2H), 7.68-7.62(m, 2H), 7.50-7.44(m, 1H), 4. 05-3.99 (m, 1H), 3.70-3.66 (m, 1H), 1.98-1.89 (m, 1H), 1.38 (d, J = 1.5Hz, 9H), 0.89 (t, J = 6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ175.8, 157.2, 139.2, 134.8, 133.0, 131.5, 128.0, 127.7, 126.8, 74.6, 35.4, 31.3, 28.9, 19.03, 19.01; HRMS (ESI) m / z: [M+H] + calculated for C 21 H 26Cl2NO2S: 426.1056, found: 426.1054; Enantiomeric excess: 88%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =7.98min(major), t R =8.46min(minor).

[0520] Example 71: Synthesis and Characterization of Compound 4bs

[0521]

[0522] The same method as in Example 1 was used to isolate the product 4bs with a yield of 71% and ee of 94%.

[0523] The structure of compound 4bs is as follows:

[0524]

[0525] Characterization data of compound 4bs:

[0526] isobutyl(R)-N-(2-naphthoyl)-4-(tert-butyl)benzenesulfinimidate 4bs: yield: 71% (28.9mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-177.3 (c 0.15CH2Cl2); 1 H NMR (600MHz, CDCl3) δ8.85 (s, 1H), 8.34 (dd, J=8.5, 1.3Hz, 1H), 8.02 (d, J=8.4Hz, 2H), 7.99 (d, J=8.0Hz, 1H), 7.88 (d, J=8.5Hz, 2H), 7.65 (d, J= 8.5Hz, 2H), 7.58-7.49 (m, 2H), 4.11 (dd, J=9.6, 6.6Hz, 1H), 3.75 (dd, J=9.6, 6.7Hz, 1H), 2.01-1.91 (m, 1H), 1.39 (s, 9H), 0.91 (t, J=6.3Hz, 6H); 13C NMR (151MHz, CDCl3) δ178.6, 156.7, 135.3, 133.7, 133.5, 132.9, 130.4, 129.5, 127.8, 127.74, 1 27.67, 127.5, 126.7, 126.2, 126.1, 74.4, 35.3, 31.3, 29.0, 19.12, 19.10; HRMS (ESI) m / z: [M+H] + calculated for C 25 H 30 NO2S: 408.1992, found: 408.1992; Enantiomeric excess: 94%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=30 / 70, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.91min(minor), t R =9.24min(major).

[0527] Example 72: Synthesis and Characterization of Compound 4bt

[0528]

[0529] The same method as in Example 1 was used to isolate the product 4bt with a yield of 80% and ee of 90%.

[0530] The structure of compound 4bt is as follows:

[0531]

[0532] Characterization data of compound 4bt:

[0533] isobutyl(R)-4-(tert-butyl)-N-(thiophene-2-carbonyl)benzenesulfinimidate 4bt: yield: 80% (29.2mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =v-365.4(c0.11CH2Cl2); 1H NMR (600MHz, CDCl3) δ7.93 (d, J=8.6Hz, 2H), 7.87 (dd, J=3.6, 1.2Hz, 1H), 7.60 (d, J=8.6Hz, 2H), 7.47 (dd, J=4.9, 1.1Hz, 1H), 7.09 (dd ; 13 C NMR (151MHz, CDCl3) δ173.4, 156.7, 141.6, 133.3, 131.6, 131.1, 127.7, 126.6, 74.1, 35.3, 31.2, 28.9, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 19 H 26 NO2S2: 364.1399, found: 364.1408; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=20 / 80, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.65min(major), t R =7.30min(minor).

[0534] Example 73: Synthesis and Characterization of Compound 4bu

[0535]

[0536] The same method as in Example 1 was used to finally separate the product 4bu with a yield of 80% and ee of 90%.

[0537] The structure of compound 4bu is as follows:

[0538]

[0539] Characterization data of compound 4bu:

[0540] isobutyl(R)-N-(4-bromothiophene-2-carbonyl)-4-(tert-butyl)benzenesulfinimidate 4bu: yield: 80% (35.4mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-132.9 (c 0.34CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.91 (d, J=8.3Hz, 2H), 7.75 (d, J=1.2Hz, 1H), 7.61 (d, J=8.3Hz, 2H), 7.36 (d, J=1.2Hz, 1H), 4.05-4.00(m, 1H), 3.67-3.62(m, 1H), 1.97-1.88(m, 1H), 1.37(d, J=0.4Hz, 9H), 0.89(t, J=6.9Hz, 6H); 13 C NMR (151MHz, CDCl3) δ172.0, 157.0, 142.6, 133.6, 132.9, 128.3, 127.7, 126.7, 110.2, 74.3, 35.4, 31.3, 28.9, 19.0; HRMS (ESI) m / z: [M+H] + calculated for C 19 H 25 BrNO2S2: 442.0505, found: 442.0510; Enantiomeric excess: 90%, determined by HPLC (Daicel Chiralpak IF, isopropanol / hexane=5 / 95, flowrate=1.0mL / min, T=30°C, λ=254nm): t R =17.0min(major), t R =17.51min(minor).

[0541] Example 74: Synthesis and Characterization of Compound 4bv

[0542]

[0543] The same method as in Example 1 was used to isolate the product 4bv with a yield of 98% and ee of 94%.

[0544] The structure of compound 4bv is as follows:

[0545]

[0546] Characterization data of compound 4bv:

[0547] isobutyl(R)-4-(tert-butyl)-N-butyrylbenzenesulfinimidate 4bv: yield: 98% (31.7mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-151.3 (c 0.04CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.81 (d, J=8.5Hz, 2H), 7.55 (d, J=8.5Hz, 2H), 3.96 (dd, J=9.6, 6.7Hz, 1H), 3.65 (dd, J=9.6, 6.7Hz, 1H), 2.51-2.44(m, 2H), 1.95-1.88(m, 1H), 1.77-1.68(m, 2H), 1.33(s, 9H), 0.97(t, J=7.4Hz, 3H), 0.88(t, J=6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ187.5, 156.5, 133.7, 127.5, 126.5, 74.5, 41.0, 35.2, 31.2, 28.9, 19.7, 19.1, 19.0, 14.1; HRMS (ESI) m / z: [M+H] + calculated for C 18 H 30 NO2S: 324.1992, found: 324.1990; Enantiomeric excess: 94%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =5.99min(major), t R =6.73min(minor).

[0548] Example 75: Synthesis and Characterization of Compound 4bw

[0549]

[0550] The same method as in Example 1 was used to finally separate the product 4bw with a yield of 88% and ee of 95%.

[0551] The structure of compound 4bw is as follows:

[0552]

[0553] Characterization data of compound 4bw:

[0554] isobutyl(R)-4-(tert-butyl)-N-isobutyrylbenzenesulfinimidate 4bw: yield: 88% (28.5mg); flash column chromatography eluent, petroleum ether / ethylacetate=10:1; colorless oil; [α] D 20 =-165.7 (c 0.03CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.82 (dd, J=8.8, 2.0Hz, 2H), 7.55 (dd, J=8.8, 2.0Hz, 2H), 3.97 (dd, J=9.7, 6.5Hz, 1H), 3.64 (dd, J= 9.7, 6.6Hz, 1H), 2.77-2.69 (m, 1H), 1.95-1.87 (m, 1H), 1.33 (s, 9H), 1.22 (dd, J=6.9, 3.8Hz, 6H), 0.88 (t, J=6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ191.3, 156.4, 133.9, 127.5, 126.5, 74.3, 37.7, 35.2, 31.2, 29.0, 20.2, 19.06, 19.05; HRMS (ESI) m / z: [M+H] + calculated for C 18 H 30 NO2S: 324.1992, found: 324.1986; Enantiomeric excess: 95%, determined by HPLC (Daicel Chiralpak AD, idopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): tR =5.49min(major), t R =6.14min(minor).

[0555] Example 76: Synthesis and Characterization of Compound 4bx

[0556]

[0557] The same method as in Example 1 was used to isolate the product 4bx with a yield of 73% and ee of 88%.

[0558] The structure of compound 4bx is as follows:

[0559]

[0560] Characterization data of compound 4bx:

[0561] isobutyl(R)-4-(tert-butyl)-N-pivaloylbenzenesulfinimidate 4bx: yield: 73% (24.5mg); flash column chromatography eluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-124.0 (c 0.05 CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.84 (d, J=8.3Hz, 2H), 7.56 (d, J=8.4Hz, 2H), 3.96 (dd, J=9.6, 6.6Hz, 1H), 3.59 (dd, J=9.6, 6.6Hz, 1H), 1.93-1.86 (m, 1H), 1.35 (s, 9H), 1.29 (s, 9H), 0.88 (t, J=7.0Hz, 6H); 13 C NMR (151MHz, CDCl3) δ192.9, 156.3, 134.1, 127.7, 126.4, 73.7, 41.1, 35.2, 31.3, 28.9, 28.4, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 19 H 31NO2S: 338.2148, found: 338.2144; Enantiomeric excess: 88%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=10 / 90, rt-ow rate=1.0mL / min, T=30°C, λ=254nm): t R =4.86min(major), t R =5.61min(minor).

[0562] Example 77: Synthesis and Characterization of Compound 4by

[0563]

[0564] The same method as in Example 1 was used to isolate the product 4by with a yield of 87% and ee of 93%.

[0565] The structure of compound 4by is as follows:

[0566]

[0567] Characterization data of compound 4by:

[0568] isobutyl(R)-4-(tert-butyl)-N-(cyclopropanecarbonyl)benzenesulfinimidate 4by: yield: 87% (28.2mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-252.3(c0.18CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.82 (d, J=8.6Hz, 2H), 7.54 (d, J=8.6Hz, 2H), 3.95 (dd, J=9.7, 6.6Hz, 1H), 3.64 (dd, J=9.7, 6.6Hz, 1 H), 1.94-1.85 (m, 2H), 1.32 (s, 9H), 1.10-1.05 (m, 1H), 1.02-0.98 (m, 1H), 0.86 (dd, J=7.8, 6.9Hz, 6H), 0.82-0.77 (m, 2H); 13CNMR (151MHz, CDCl3) δ187.6, 156.5, 133.8, 127.5, 126.5, 74.5, 35.2, 31.2, 28.9, 19.02, 18.99, 17.4, 9.4, 8.7; HRMS (ESI) m / z: [M+H] + calculated for C 18 H 28 NO2S: 322.1835, found: 322.1835; Enantiomeric excess: 93%, determined by HPLC (Daicel ChiralpakAD, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.56min(major), t R =7.10min(minor).

[0569] Example 78: Synthesis and Characterization of Compound 4bz

[0570]

[0571] The same method as in Example 1 was used to isolate the product 4bz with a yield of 97% and ee of 94%.

[0572] The structure of compound 4bz is as follows:

[0573]

[0574] Characterization data of compound 4bz:

[0575] isobutyl(R)-4-(tert-butyl)-N-(cyclohexanecarbonyl)benzenesulfinimidate 4bz: yield: 97% (35.1mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-182.9(c0.28CH2Cl2); 1H NMR (600MHz, CDCl3) δ7.82 (d, J=8.5Hz, 2H), 7.55 (d, J=8.5Hz, 2H), 3.96 (dd, J=9.7, 6.6Hz, 1H), 3.64 (dd, J=9.7, 6.6Hz, 1H), 2.04-1.96 (m, 2 H), 1.94-1.87(m, 1H), 1.81-1.73(m, 2H), 1.69-1.62(m, 1H), 1.56-1.4 8(m, 2H), 1.37-1.32(m, 9H), 1.30-1.23(m, 4H), 0.88(t, J=6.7Hz, 6H); 13 C NMR (151MHz, CDCl3) δ190.3, 156.4, 134.0, 127.5, 126.5, 74.3, 47.4, 35.2, 31. 3, 30.33, 30.31, 29.0, 26.2, 26.12, 26.07, 19.09, 19.07; HRMS(ESI)m / z: [M+H] + calculated for C 21 H 34 NO2S: 364.2305, found: 364.2303; Enantiomeric excess: 94%, determined by HPLC (Daicel Chiralpak AD, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =6.07min(major), t R =7.17min(minor).

[0576] Example 79: Synthesis and Characterization of Compound 4ca

[0577]

[0578] The same method as in Example 1 was used to isolate the product 4ca with a yield of 84% and ee of 63%.

[0579] The structure of compound 4ca is as follows:

[0580]

[0581] Characterization data of compound 4ca:

[0582] isobutyl(R)-4-(tert-butyl)-N-(p-tolylcarbamoyl)benzenesulfinimidate4ca: yield: 84% (32.3mg); flash column chromatographyeluent, petroleum ether / ethyl acetate=10:1; colorless oil; [α] D 20 =-38.1(c0.32CH2Cl2); 1 H NMR (600MHz, CDCl3) δ7.82 (d, J=8.4Hz, 2H), 7.55 (d, J=8.4Hz, 2H), 7.38 (d, J=7.7Hz, 2H), 7.28 (s, 1H), 7.08 (d, J=8.0Hz, 2H), 4.01 (dd, J=9.5, 6.6Hz, 1H), 3.78-3.66 (m, 1H), 2.29 (s, 3H), 2.02-1.90 (m, 1H), 1.34 (s, 9H), 0.91 (t, J=6.5Hz, 6H); 13 C NMR (151MHz, CDCl3) δ163.3, 156.2, 137.1, 134.3, 132.0, 129.4, 127.2, 126.5, 118.9, 73.9, 35.2, 31.2, 29.0, 20.8, 19.1; HRMS (ESI) m / z: [M+H] + calculated for C 22 H 31 N2O2S: 387.2106, found: 387.2108; Enantiomeric excess: 63%, determined by HPLC (DaicelChiralpak IF, isopropanol / hexane=10 / 90, flow rate=1.0mL / min, T=30°C, λ=254nm): t R =21.78min(major), t R =23.93min(minor).

[0583] Table 1 Synthesis of chiral sulfilimine esters in the present invention

[0584]

[0585]

[0586]

[0587]

[0588]

[0589] 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, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the scope of protection of the present invention.

[0590] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any appropriate manner without contradiction. In order to avoid unnecessary repetition, the present invention will not further describe various possible combinations.

[0591] In addition, the 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. A chiral sulfilimine lipid compound, characterized in that: The general structural formula of the chiral sulfilimine lipid compound is: Among them, R 1 C 1-8 Straight chain or branched alkyl / cycloalkyl / alkynyl, C3 halogenated straight chain alkyl, C 6-9 One of aryl or substituted aryl, naphthyl; The substituted aryl group is C 1-3 One of an alkyl-substituted aryl group, a C2 oxyalkyl-substituted aryl group, a nitro-substituted phenethyl group, a trifluoromethyl-substituted benzyl group or a halogenated benzyl group; R 2 is n-butyl or cyclohexyl, C 6-9 one of aryl, benzyl, substituted aryl, substituted benzyl or thienyl; The substituted aryl group is one of a methyl or isopropyl substituted aryl group, a cyano substituted aryl group, a methyl formate substituted aryl group, a nitro substituted aryl group, a methoxy substituted aryl group, a trifluoromethyl substituted aryl group or a halogenated aryl group; the substituted benzyl group is a methyl substituted benzyl group; R 3 C 3 / 4 / 6 Straight chain or branched alkyl / cycloalkyl, C 6-8 One of substituted aryl, naphthyl, thienyl or 4-methylanilino; The substituted aryl group is one of a cyano-substituted aryl group, a trifluoromethyl-substituted aryl group, a nitro-substituted aryl group, a methylformyl-substituted aryl group, a benzoyl-substituted aryl group, a methyl-substituted aryl group, a methoxy-substituted aryl group or a halogenated aryl group.

2. The chiral sulfilimine lipid compound according to claim 1, wherein R 1 Alkyl is one of methyl, ethyl, n-propyl, isopropyl, isobutyl, 3-pentyl, n-hexyl, n-octyl or p-cholesteryl; Cycloalkyl is one of cyclopropylmethyl, cyclobutyl, cyclohexyl, cyclopentylethyl or cyclohexylethyl; Alkynyl is one of 2-butynyl, 3-butynyl and 4-pentynyl; halogen is one of fluorine, chlorine and bromine.

3. The chiral sulfilimine lipid compound according to claim 1, wherein R 2 Halogen is one of fluorine, chlorine or bromine.

4. The chiral sulfilimine lipid compound according to claim 1, wherein R 3 The alkyl group is one of n-propyl, isopropyl or tert-butyl; Cycloalkyl is one of cyclopropyl or cyclohexyl; Halogen is one of fluorine, chlorine or bromine.

5. The method for preparing a chiral sulfilimine lipid compound according to any one of claims 1 to 4, characterized in that: The preparation method comprises: 1) Sulfenamide (Formula 2), alcohol (Formula 3), MS, metal-centered chiral cobalt (III) complex anion, and ultra-dry tetrahydrofuran were mixed and reacted at -45°C to -35°C for 25-35 minutes; 2) N-iodosuccinimide is then added, and the entire system is reacted at -45°C to -35°C for 35-37 hours. A Na2S2O3 aqueous solution is added, and the organic layer is separated from the aqueous phase to quench the reaction. The chiral sulfilimine lipid compound (Formula 4) is isolated and purified.

6. The preparation method according to claim 5, wherein In step (2), after the reaction is quenched, the aqueous phase is extracted with ethyl acetate (3×5.0 mL), the organic layer is dried over Na 2 SO 4 , concentrated under reduced pressure, and purified by column chromatography using a mixture of petroleum ether / ethyl acetate (10 / 1) as eluent to obtain a chiral sulfilimine lipid compound.

7. The preparation method according to claim 5 or 6, wherein Relative to 0.10mmol of sulfenamide, the amount of isobutanol used is 0.15-0.25mmol, the amount of metal-centered chiral cobalt (III) complex anion used is 0.005-0.015mmol, and the amount of N-iodosuccinimide used is 0.15-0.25mmol. The amount of MS used is 95-105 mg, and the amount of tetrahydrofuran used is 0.05-0.15 mL.

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

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