Synthesis method of chiral sulfonyl substituted vinyl naphthalene axial chiral compound

Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of a chiral sulfonyl substituted vinyl naphthalene axial chiral compound. The method comprises the following steps: in a solvent, under a mild condition, generating a sulfinic acid anion intermediate from a cyclopropanol compound and a sulfur dioxide solid substitute in situ, and then carrying out asymmetric nucleophilic attack on a 1-alkynyl-2-naphthol compound activated by a chiral small organic molecule catalyst, so as to obtain the 1-alkynyl-2-naphthol compound. The chiral sulfonyl substituted vinyl naphthalene axial chiral compound is obtained. The synthesis method has the advantages that the conditions are mild, the method is simple and efficient, the application range of substrates is wide, the high-enantioselectivity sulfonyl substituted vinyl naphthalene axial chiral compound is obtained, the types of sulfonylation reactions are enriched to a certain extent, and the method has good application value.

Description

Technical Field

[0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound. Background Art

[0002] Axially chiral compounds are an important class of chiral-dominant skeletons. Chiral catalysts and chiral ligands based on this structure have a wide range of applications in asymmetric catalysis [(a) Mori, K.; Ohmori, K.; Suzuki, K. Angew. Chem. Int. Ed. 2009, 48, 5633; (b) Mori, K.; Ohmori, K.; Suzuki, K. Angew. Chem. Int. Ed. 2009, 48, 5638; (c) Glorius, F. Angew. Chem. Int. Ed. 2004, 43, 3364; (d) Nagamoto, M.; Nishimura, T. ACS Catal. 2017, 7(1), 833.]. Compared with the established axially chiral skeletons of biphenyl or binaphthyl structures, the asymmetric synthesis of axially chiral styrene catalyzed by acyclic olefins has been less studied because of its lower rotation barrier and more flexible skeleton. In 2017, Tan Bin and his colleagues reported a pioneering work on the construction of axial chiral styrenes on acetylenes through organocatalytic asymmetric nucleophilic addition (Nagamoto, M.; Nishimura, T. ACS Catal. 2017, 7, 833–847.). Subsequently, several strategies for obtaining axial chiral styrenes were developed [(a) Zhang, C.; Tang, Z.; Qiu, Y.; Tang, J.; Ye, S.; Li, Z.; Wu, J. Chem Catal.2022,2,164–177; (b) Yang, C.; Wu, T.-R.; Li, Y.; Wu, B.-B.; Jin, R.-X.; Hu, D.-D.; Li, Y.-B.; Bian, K.-J.; Wang, X.-S. Chem. Sci.2021,12,3726; (c) Song, H.; Li, Y.; Yao, Q.; Jin, L.; Liu, L.; Liu, Y.; Shi, B. Angew. Chem. Int. Ed.2020,59,6576. (d) Zhang, C.; Ye, S.; Wu, J. Org. Lett.2024,26,3321]. However, there are many problems such as cumbersome steps, harsh conditions and restricted functional groups. Summary of the invention

[0003] The present invention aims to solve the above technical problems and provide a simple and efficient method for synthesizing sulfonyl-substituted axial chiral compounds.

[0004] The method for synthesizing a sulfonyl-substituted axial chiral compound provided by the present invention is to utilize a 1-alkynyl-2-naphthol compound, a sulfur dioxide solid substitute and a cyclopropanol compound to react in a solvent under mild conditions under the action of a chiral organic small molecule catalyst to efficiently construct a sulfonyl-substituted axial chiral compound.

[0005] The technical solutions adopted by the present invention to solve the above technical problems are as follows:

[0006] A method for synthesizing a chiral sulfonyl-substituted vinyl naphthalene axial chiral compound, the method of the invention is to react a 1-alkynyl-2-naphthol compound (Formula I), a sulfur dioxide solid substitute (Formula II) and a cyclopropanol compound (Formula III) under mild conditions in a solvent (Solvent) under the action of a chiral organic small molecule catalyst (Cat) to obtain a target chiral sulfonyl-substituted vinyl naphthalene axial chiral compound (Formula IV), the reaction formula of the reaction is shown below. In the present invention, the cyclopropanol compound and the sulfur dioxide solid substitute generate a sulfinic acid anion intermediate in situ under mild conditions, and then a 1-alkynyl-2-naphthol compound activated by the chiral organic small molecule catalyst is subjected to an asymmetric nucleophilic attack to obtain the target sulfonyl-substituted vinyl naphthalene axial chiral compound.

[0007] The reaction formula is:

[0008]

[0009] In the formula, R is selected from at least one of H and C1-C6 alkoxy;

[0010] R 1 is selected from aryl groups substituted or unsubstituted by substituents; wherein the aryl group is selected from at least one of phenyl and thienyl, and the substituent is selected from at least one of C1-C6 alkyl, C1-C6 alkoxy, halogen group, phenyl, and p-ethoxybenzyl; the halogen group includes at least one of F, Cl, Br, and I;

[0011] R 2 At least one selected from substituted or unsubstituted benzyl, substituted or unsubstituted aryl, substituted or unsubstituted C1-C12 alkyl, and C1-C6 cycloalkyl; wherein the aryl is selected from at least one of phenyl, naphthyl, and thienyl; the substituent is selected from at least one of C1-C6 alkyl, C1-C6 alkoxy, trifluoromethyl, thienyl, phenyl, and a halogen group; the halogen group includes at least one of F, Cl, Br, and I.

[0012] Preferably, the chiral organic small molecule catalyst comprises at least one of the following structural formulas:

[0013]

[0014] More preferably, the chiral organic small molecule catalyst includes at least one of the structural formulas A, B, C, D, and E.

[0015] Preferably, in the present invention, the solvent used is at least one of water, trifluorotoluene, hexafluoroisopropanol, saturated sodium chloride solution, saturated potassium chloride solution, and saturated ammonium chloride solution. More preferably, the solvent is at least one of a mixed solvent of water and trifluorotoluene, and a mixed solvent of water and hexafluoroisopropanol. More preferably, it is a mixed solvent of water and trifluorotoluene, and more preferably the volume ratio of water to trifluorotoluene is 1:1-9, and more preferably the volume ratio is 1:1. The above solvents can all carry out the reaction described in the present application and obtain good yields and ee values, and the reaction yield and ee value can be further improved in a mixed solution of water and trifluorotoluene.

[0016] Preferably, in the present invention, the solid sulfur dioxide substitute used is at least one of Na2S2O5, DABCO·(SO2)2(DABSO), NaHSO3 and K2S2O5. More preferably, it is K2S2O5, which can further improve the reaction yield compared with other solid sulfur dioxide substitutes.

[0017] Preferably, in the present invention, the molar ratio of 1-alkynyl-2-naphthol compound, sulfur dioxide solid substitute, cyclopropanol compound, and chiral organic small molecule catalyst is 1:1.0-3.0:1.0-3.0:0.01-0.02, more preferably 1:1.5:2:0.01, and the reaction yield can be further improved.

[0018] Preferably, in the present invention, the reaction is further added with an additive, and the additive used is at least one of boric acid (H3BO3), acetic acid (AcOH), and p-toluenesulfonic acid monohydrate (TsOH·H2O). More preferably, p-toluenesulfonic acid monohydrate (TsOH·H2O) can further improve the reaction yield compared to other additives. More preferably, the molar ratio of the amount of the additive to the 1-alkynyl-2-naphthol compound is 1-2:1, more preferably 1.5:1.

[0019] Preferably, in the present invention, the reaction temperature is 10-50°C, more preferably 20°C, and the reaction can further improve the yield.

[0020] Preferably, in the present invention, whether the reaction is complete is monitored by TLC, and more preferably the reaction time is 24-48 h.

[0021] Preferably, the reaction of the present invention is carried out under anaerobic conditions, and the anaerobic conditions are achieved by inert gas protection, and the inert gas is preferably at least one of nitrogen, helium and argon.

[0022] Preferably, the specific steps of the method of the present invention include the following:

[0023] (1) under anaerobic conditions, a chiral organic small molecule catalyst, a sulfur dioxide solid substitute, a 1-alkynyl-2-naphthol compound, and a cyclopropanol compound are sequentially added to a reaction tube, and a solvent is added after the reaction system is in anaerobic conditions, and the mixture is stirred until the reaction is complete;

[0024] (2) After the reaction is completed, the product is separated and purified to obtain a pure corresponding sulfonyl-substituted vinylnaphthalene axial chiral compound.

[0025] More preferably, the reaction system is in an anaerobic condition by replacing the reaction tube with an inert gas.

[0026] More preferably, after the reaction is completed as monitored by TLC, the reaction solution is dried with a common drying agent such as anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography using a mixed system of petroleum ether and ethyl acetate as the mobile phase for separation and purification.

[0027] More preferably, the yield of the above reaction can reach above 70%, and the ee value of the target chiral sulfonyl-substituted vinylnaphthalene axial chiral compound can reach above 98%.

[0028] More preferably, the structure of the sulfonyl-substituted vinylnaphthalene axial chiral compound prepared by the present invention is 1 HNMR, 13 The product was characterized and confirmed by C NMR and other methods, and the ee value was detected by chiral HPLC.

[0029] Compared with the prior art, the beneficial effects of the present invention are as follows: the method of the present invention is to generate a sulfinic acid anion intermediate in situ from a cyclopropanol compound and a solid substitute for sulfur dioxide such as sodium pyrosulfite (K2S2O5) under mild and simple conditions, and then to perform an asymmetric nucleophilic attack on a 1-alkynyl-2-naphthol compound activated by a chiral organic small molecule catalyst to obtain a sulfonyl-substituted vinyl naphthalene axial chiral compound. The advantages of the preparation method of the sulfonyl-substituted vinyl naphthalene axial chiral compound of the present invention are mild conditions, simplicity and high efficiency, and a wide range of substrate applications. High enantioselective sulfonyl-substituted vinyl naphthalene axial chiral compounds are obtained, which enriches the types of sulfonylation reactions to a certain extent and has good application value. Moreover, the solid substitutes for sulfur dioxide used in the method are all abundant and easily available chemical raw materials, which avoids the use of strong acidic raw materials in the synthesis of traditional sulfonyl compounds, and provides a simple and efficient way to construct a series of sulfonyl-substituted vinyl naphthalene axial chiral compounds, which has good guiding significance and application prospects in academic research and industrial fields. DETAILED DESCRIPTION

[0030] In order to better clarify and understand the purpose, process scheme and advantages of the present invention, the technical scheme and implementation method of the present invention are further described clearly, completely and in detail through specific examples. It should be noted that the embodiments described in the present invention are implemented on the premise of the technical scheme of the present invention, and detailed implementation methods and specific operation processes are given, but they are only part of the embodiments of the present invention, not all of the embodiments. The specific implementation methods described are limited to explaining and interpreting the present invention, and do not limit the present invention. Based on the embodiments in the present invention, all other implementation methods obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0031] The experimental methods and conditions used in the following examples are conventional methods and conventional conditions unless otherwise specified. The materials, reagents or instruments used in the examples, unless otherwise specified, can be obtained from commercial sources or prepared by conventional methods. The reaction conditions embodied in the content of the invention of the present invention can achieve the reaction and obtain the product with the expected effect. Due to space limitations, some embodiments are listed below to further illustrate the advantages of the technical solution of the present invention.

[0032] Example 1

[0033]

[0034] At room temperature, 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-10,11-dihydro-6'-methoxyquinin-9-yl]amino]-3-cyclobutane-1,2-dione (0.01 mmol), potassium pyrosulfite (0.15 mmol), 1-phenylethynyl)naphthalen-2-ol (0.1 mmol), p-toluenesulfonic acid hydrate (0.15 mmol), and benzylcyclopropanol (0.2 mmol) were added to a dry reaction tube in sequence. The reaction tube was plugged with a stopper and replaced with high-purity nitrogen or argon three times to make the system under anaerobic conditions. Trifluorotoluene (1 ml) and water (1 ml) were added, and the mixture was stirred at 20°C until the reaction was complete as monitored by TLC. The reaction solution was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding sulfonyl-substituted vinylnaphthalene axial chiral compound Example 1 as a white solid with a yield of 70% and an ee value of 98%.

[0035] Structural characterization of compound example 1: 1HNMR (400MHz, CDCl3) δ (ppm) 8.11 (s, 1H), 7.88 (d, J = 9.2Hz, 1H), 7.81–7.77 (m, 1H), 7.57–7.51 (m, 2H), 7.34–7.23 (m, 6H) ,7.18(t,J=7.2Hz,1H),7.11–7.04(m,4H),6.97(d,J=7.6Hz,2H),3.64(s,2H),3.19(t,J=7.2Hz,2H),2.98–2.82(m,2H); 13 C NMR (100MHz, CDCl3) δ (ppm) 204.1, 153.7, 143.7, 133.2, 132.8, 132.6, 132.06, 132.0, 131.0, 130. 4,129.4,129.4,128.9,128.8,128.7,128.0,127.4,124.3,123.0,119.9,110.4,49.9,45.9,33.8;

[0036] Examples 1-26

[0037] On the basis of Example 1, the reactants were replaced to react and the corresponding sulfonyl-substituted vinylnaphthalene axial chiral compounds were obtained. The details are shown in Table 1 below:

[0038] Table 1 Summary of reactants, products and results of Examples 1-29

[0039]

[0040]

[0041]

[0042]

[0043]

[0044] The products obtained in the above Table 1 have all been structurally verified by corresponding detection means. Due to space limitations, only specific reactants, products and corresponding characterization data of some examples in Table 1 are listed below for reference.

[0045] Example 10

[0046]

[0047] At room temperature, 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-10,11-dihydro-6'-methoxyquinin-9-yl]amino]-3-cyclobutane-1,2-dione (0.01mmol), potassium pyrosulfite (0.15mmol), 1-((2-chlorophenyl)ethynyl)naphthalen-2-ol (0.1mmol)(0.1mmol), p-toluenesulfonic acid hydrate (0.15mmol), and benzylcyclopropanol (0.2mmol) were added to a dry reaction tube in sequence. The reaction tube was plugged with a stopper and replaced with high-purity nitrogen or argon three times to make the system under anaerobic conditions. Trifluorotoluene (1ml) and water (1ml) were added, and the system was stirred at 20°C until the reaction was complete as monitored by TLC. The reaction solution was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding chiral sulfonyl-substituted vinylnaphthalene axial chiral compound Example 10 as a white solid with a yield of 56% and an ee value of 98%.

[0048] Structural characterization of compound example 10: 1 HNMR(400MHz, CDCl3)δ(ppm)8.47(s,1H),7.81(d,J=8.8Hz,1H),7.72(d,J=7.2Hz,1H),7.64(s,1H),7.49(d,J=8.0Hz,1H),7.34–7.25(m,6 H),7.22(d,J=8.8Hz,1H),7.11(d,J=6.4Hz,2H),7.08–7.03(m,1H),6.76–6.70(m,2H),3.66(s,2H),3.23–3.15(m,2H),2.96–2.91(m,2H); 13 C NMR (100MHz, CDCl3) δ (ppm) 203.89, 154.4, 141.3, 135.7, 135.0, 133.1, 132.6, 131.9, 131.39, 130.8, 129. 5,129.4,129.3,129.2,128.9,128.7,127.9,127.4,126.7,124.2,122.7,119.6,109.9,50.0,45.9,33.8.

[0049] Embodiment 13

[0050]

[0051] At room temperature, 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-10,11-dihydro-6'-methoxyquinin-9-yl]amino]-3-cyclobutane-1,2-dione (0.01mmol), potassium pyrosulfite (0.15mmol), 1-(thiophene-2-ethynyl)naphthalen-2-ol (0.1mmol), p-toluenesulfonic acid hydrate (0.15mmol), and benzylcyclopropanol (0.2mmol) were added to a dry reaction tube in sequence. The reaction tube was plugged with a stopper and replaced with high-purity nitrogen or argon three times to make the system under anaerobic conditions. Trifluorotoluene (1ml) and water (1ml) were added, and the system was stirred at 20°C until the reaction was complete as monitored by TLC. The reaction solution was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography using a mixture of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding chiral sulfonyl-substituted vinylnaphthalene axial chiral compound Example 13. White solid, yield 63%, ee value 99%.

[0052] Structural characterization of compound example 13: 1 HNMR (400MHz, CDCl3) δ (ppm) 8.12 (s, 1H), 7.91 (d, J = 8.8Hz, 1H), 7.84–7.8 1(m,1H),7.56–7.54(m,1H),7.50(s,1H),7.37–7.33(m,2H),7.32–7.25(m, 4H),7.15–7.14(m,1H),7.11–7.09(m,2H),6.95(dd,J=5.2,3.2Hz,1H),6. 25(d,J=5.2Hz,1H),3.65(s,2H),3.21(t,J=7.2Hz,2H),3.00–2.84(m,2H); 13 C NMR (100MHz, CDCl3) δ (ppm) 204.0,153.7,137.3,134.1,133.1,132.6,132.3,132.1,130. 7,129.4,128.9,128.8,128.1,127.4,126.5,124.3,123.0,120.0,110.5,50.0,46.1,33.7

[0053] Embodiment 23

[0054]

[0055] At room temperature, 3-[[3,5-bis(trifluoromethyl)phenyl]amino]-4-[[(8α,9S)-10,11-dihydro-6'-methoxyquinin-9-yl]amino]-3-cyclobutane-1,2-dione (0.01 mmol), potassium pyrosulfite (0.15 mmol), (1-(phenylethynyl)naphthalen-2-ol (0.1 mmol), p-toluenesulfonic acid hydrate (0.15 mmol), 1-(4-methoxyphenyl)cyclopropane-1-ol were added to a dry reaction tube in sequence. (0.02mmol), plug the reaction tube with a stopper and replace it with high-purity nitrogen or argon three times to make the system in anoxic conditions, then add trifluorotoluene (1ml) and water (1ml), stir at 20°C until the reaction is complete as monitored by TLC. The reaction solution is dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography using a mixed system of petroleum ether and ethyl acetate as the mobile phase to obtain the corresponding chiral sulfonyl-substituted vinylnaphthalene axial chiral compound Example 23. White solid, yield 55%, ee value 98%

[0056] Structural characterization of compound example 23: 1 HNMR(400MHz, CDCl3)δ(ppm)8.17(s,1H),7.91(d,J=8.8Hz,1H),7.84–7.76(m,4H),7.64(d,J=8.0Hz,1H),7.38–7.29(m,3H) ,7.20(t,J=7.6Hz,1H),7.08(t,J=8.0Hz,2H),7.01(d,J=7.2Hz,2H),6.89(d,J=9.2Hz,2H),3.85(s,3H),3.46–3.37(m,4H); 13 C NMR (100MHz, CDCl3) δ (ppm) 194.2, 164.0, 153.8, 143.7, 133.1, 132.6, 132.1, 130.9, 130.5 ,130.4,129.5,128.8,128.7,128.0,124.3,123.2,119.9,113.9,110.5,55.5,46.5,30.4;

[0057] Embodiment 26-52

[0058] On the basis of Example 1, the reaction conditions were changed, including changing the chiral organic small molecule catalyst, changing the solvent, changing the sulfur dioxide solid substitute, changing the feed ratio, changing the reaction temperature, etc., as shown in Table 2 below:

[0059]

[0060] Table 2 Summary of reaction conditions for Examples 1, 26-52

[0061]

[0062]

[0063]

[0064] Among them, the structural formula of the chiral organic small molecule catalyst is as follows:

[0065]

[0066] It can be seen from the above results that, after a large number of experiments, the present invention has obtained a method for preparing the target sulfonyl-substituted axial chiral vinyl naphthalene compound, which has mild conditions, is simple and efficient, has cheap and readily available raw materials, and has a wide range of substrate applicability, and is of great significance to the related fields of asymmetric sulfone compounds.

[0067] Those skilled in the art should recognize that the above examples are only used to illustrate the present invention, and are not intended to limit the present invention. As long as they are within the spirit of the present invention, any changes or modifications to the above-described embodiments will fall within the scope of the claims of the present invention.

Claims

1. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound, characterized in that: The method comprises reacting a 1-alkynyl-2-naphthol compound (Formula I), a sulfur dioxide solid substitute (Formula II) and a cyclopropanol compound (Formula III) in a solvent under the action of a chiral organic small molecule catalyst under mild conditions to obtain a target sulfonyl-substituted vinylnaphthalene axial chiral compound (Formula IV). The reaction formula of the reaction is shown below: In the formula, R is selected from at least one of H and C1-C6 alkoxy; R 1 is selected from aryl groups substituted or unsubstituted by substituents; wherein the aryl group is selected from at least one of phenyl and thienyl, and the substituent is selected from at least one of C1-C6 alkyl, C1-C6 alkoxy, halogen group, phenyl, and p-ethoxybenzyl; the halogen group includes at least one of F, Cl, Br, and I; R 2 At least one selected from substituted or unsubstituted benzyl, substituted or unsubstituted aryl, substituted or unsubstituted C1-C12 alkyl, and C1-C6 cycloalkyl; wherein the aryl is selected from at least one of phenyl, naphthyl, and thienyl; the substituent is selected from at least one of C1-C6 alkyl, C1-C6 alkoxy, trifluoromethyl, thienyl, phenyl, and a halogen group; the halogen group includes at least one of F, Cl, Br, and I.

2. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 1, characterized in that: The chiral organic small molecule catalyst includes at least one of the following formulas:

3. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 1, characterized in that: The solvent is at least one of water, trifluorotoluene, methanol, ethanol, hexafluoroisopropanol, saturated sodium chloride solution, saturated potassium chloride solution, and saturated ammonium chloride solution.

4. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 3, characterized in that: The solvent is at least one of a mixed solvent of water and trifluorotoluene and a mixed solvent of water and hexafluoroisopropanol.

5. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 1, characterized in that: The solid sulfur dioxide substitute is at least one of Na2S2O5, DABCO·(SO2)2, NaHSO3 and K2S2O5.

6. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 1, characterized in that: The feeding molar ratio of 1-alkynyl-2-naphthol compound, solid sulfur dioxide substitute, cyclopropanol compound and chiral organic small molecule catalyst is 1:1.0-3.0:1.0-3.0:0.01-0.

02.

7. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 6, characterized in that: The feeding molar ratio of 1-alkynyl-2-naphthol compound, sulfur dioxide solid substitute, cyclopropanol compound and chiral organic small molecule catalyst is 1:1.5:2:0.

01.

8. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 1, characterized in that: The reaction is further added with an additive, wherein the additive is at least one of boric acid, acetic acid and p-toluenesulfonic acid monohydrate; the molar ratio of the additive to the 1-alkynyl-2-naphthol compound is 1-2:

1.

9. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound as claimed in claim 1, characterized in that: The reaction temperature is 10°C to 50°C.

10. A method for synthesizing a chiral sulfonyl-substituted vinylnaphthalene axial chiral compound according to any one of claims 1 to 9, characterized in that: The specific steps of the method of the present invention include the following: (1) under anaerobic conditions, adding a chiral organic small molecule catalyst, a solid sulfur dioxide substitute, a 1-alkynyl-2-naphthol compound, and a cyclopropanol compound to a reaction tube, adding a solvent after the reaction system is in anaerobic conditions, and stirring until the reaction is complete; (2) After the reaction is completed, the product is separated and purified to obtain a pure corresponding sulfonyl-substituted vinylnaphthalene axial chiral compound.

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