Sulfoxide-oxazoline ligand compound based on ferrocene skeleton as well as preparation method and application of sulfoxide-oxazoline ligand compound

Abstract

The invention discloses a sulfoxide-oxazoline ligand compound based on a ferrocene skeleton as well as a preparation method and application of the sulfoxide-oxazoline ligand compound. The novel sulfoxide-oxazoline ligand with the ferrocene framework is suitable for catalyzing organic reaction, and particularly shows excellent performance in asymmetric reaction catalyzed by metal when being used as a chiral oxazoline ligand. In the field of asymmetric catalysis, the ligand can effectively guide chiral control of a product and improve the optical purity of a target product, is crucial to synthesis of fine chemicals, medical intermediates and new materials, and has economic practicability and industrial application prospects.

Description

Technical Field

[0001] The invention relates to the technical field of organic chemistry, and relates to a novel sulfoxide-oxazoline ligand compound based on a ferrocene skeleton, a preparation method and application thereof. The ligand can be used for coupling reaction or asymmetric catalytic reaction. Background Art

[0002] In the past few decades, the field of asymmetric catalysis has experienced unprecedented development. During this process, chemists have synthesized numerous chiral ligands and widely used them in asymmetric catalytic reactions. These chiral ligands are of various types, including bisphosphine ligands, oxazoline-phosphine ligands, bisoxazoline ligands, phosphine-sulfur ligands, etc. These chiral ligands show excellent enantioselectivity and diastereoselectivity in asymmetric catalytic reactions, covering a variety of reaction types such as asymmetric hydrogenation, Michael addition, and asymmetric cycloaddition.

[0003] It is particularly worth mentioning that the sulfoxide-oxazoline ligand synthesized by the White group (SirJames LKWhite) achieved extremely high chemical selectivity and enantioselectivity in asymmetric carbon-hydrogen bond activation reactions, providing an important reference for research in related fields.

[0004] Although the existing chiral ligands have reached a rich level in types and quantity, each different ligand skeleton exhibits its own unique properties and catalytic behavior. The application of these ligands is often subject to certain limitations, which is reflected in their strong dependence on specific reaction substrates and relatively narrow scope of application. Therefore, a chiral ligand that can be universally applied to various reactions has not yet been found. In this context, seeking and creating chiral ligands with innovative skeleton structures has always been the purpose and continuous research direction pursued in catalytic asymmetric synthesis research. Summary of the invention

[0005] 1. Technical issues to be resolved

[0006] The purpose of the present invention is to provide a sulfoxide-oxazoline ligand compound based on a ferrocene skeleton and a preparation method and application thereof.

[0007] (II) Technical solution

[0008] A sulfoxide-oxazoline ligand based on a ferrocene skeleton is a compound having the following general formula I or an enantiomer, racemate or diastereoisomer of the compound:

[0009]

[0010] In each formula: In each formula: R is methyl, ethyl, isopropyl, tert-butyl, benzyl, cyclohexyl, isobutyl, phenyl, p-fluorophenyl, p-tert-butylphenyl or 3,5-di-tert-butylphenyl; Ar is tolyl, p-tert-butylphenyl or p-trifluoromethylphenyl.

[0011] Preferably, the compound as shown in general formula I is selected from any of the following compounds:

[0012]

[0013] In each formula: R is methyl, ethyl, isopropyl, tert-butyl, benzyl, cyclohexyl, isobutyl, phenyl, p-fluorophenyl, p-tert-butylphenyl or 3,5-di-tert-butylphenyl; Ar is tolyl, p-tert-butylphenyl or p-trifluoromethylphenyl.

[0014] Preferably, the compound represented by general formula I is selected from any one of target compounds 1 to 3:

[0015]

[0016] Preferably, the preparation method of target compound 1 is:

[0017] S1: (S)-(5-tert-butyloxazolidinediyl)ferrocene was added with TMEDA and methyl tert-butyl ether under argon atmosphere;

[0018] S2: n-Butyl lithium was added dropwise in a dry ice bath, and then reacted at -78°C for 30 min, and then in an ice bath for 60 min;

[0019] S3: (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed;

[0020] S4: After the reaction is completed, water is added to quench the mixture, and ethyl acetate is added to extract the mixture, followed by drying with anhydrous sodium sulfate, and then purification by column chromatography with ethyl acetate and petroleum ether to obtain the target compound 1;

[0021] The synthetic route is as follows:

[0022]

[0023] Preferably, the preparation method of target compound 2 is:

[0024] S1: (4S)-tert-butyl-(2Rp)-[2-(Rs)-(p-tolylsulfoxide)ferrocenyl]-2-oxazoline was added with TMEDA and methyl tert-butyl ether under argon atmosphere;

[0025] S2: n-Butyl lithium was added dropwise in a dry ice bath, and then reacted at -78°C for 30 min, and then in an ice bath for 60 min;

[0026] S3: (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed;

[0027] S4: After the reaction is completed, water is added to quench, and ethyl acetate is added to extract, and the mixture is dried over anhydrous sodium sulfate, and then the mixture is dried by rotary evaporation and purified by column chromatography with ethyl acetate and petroleum ether to obtain a yellow oil;

[0028] S5: The yellow oily product of step S4 is placed in a round-bottom flask, and tetramethylammonium fluoride and tetrahydrofuran are added under an argon atmosphere;

[0029] S6: Stirring in an oil bath at 50°C until the reaction is complete, drying by rotary evaporation, and then purifying by ethyl acetate and petroleum ether column chromatography to obtain the target compound II;

[0030] The synthetic route is as follows:

[0031]

[0032] Preferably, the preparation method of target compound three is:

[0033] S1: (R)-(5-tert-butyloxazolidinediyl)ferrocene was added with TMEDA and methyl tert-butyl ether under argon atmosphere;

[0034] S2: n-Butyl lithium was added dropwise in a dry ice bath, and then reacted at -78°C for 30 min, and then in an ice bath for 60 min;

[0035] S3: (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed;

[0036] S4: After the reaction is completed, water is added to quench, ethyl acetate is added to extract, and the mixture is dried over anhydrous sodium sulfate. After being dried by a rotary evaporator, the mixture is purified by column chromatography using ethyl acetate and petroleum ether to obtain the target compound three;

[0037] The synthetic route is as follows:

[0038]

[0039] The invention discloses a use of a sulfoxide-oxazoline ligand based on a ferrocene skeleton. The sulfoxide-oxazoline ligand based on a ferrocene skeleton is complexed with a metal salt of iron, gold, silver, copper, zinc, magnesium, rhodium, ruthenium, nickel, molybdenum, palladium or cobalt to prepare a catalyst.

[0040] The invention discloses the use of the sulfoxide-oxazoline ligand based on a ferrocene skeleton. The sulfoxide-oxazoline ligand based on a ferrocene skeleton is used as a catalyst ligand in metal-catalyzed coupling reactions, insertion reactions and asymmetric reactions.

[0041] Furthermore, the sulfoxide-oxazoline ligand based on the ferrocene skeleton is used for metal-catalyzed asymmetric Friedel-Crafts alkylation reaction and asymmetric NH, OH, SH, Si-H or CH insertion reaction.

[0042] The invention discloses the use of the sulfoxide-oxazoline ligand based on a ferrocene skeleton, and the use of the sulfoxide-oxazoline ligand based on a ferrocene skeleton as a chiral reagent in a drug / oseltamivir synthesis process.

[0043] (III) Beneficial effects

[0044] This new ferrocene skeleton sulfoxide-oxazoline ligand is suitable for catalyzing organic reactions, especially as a chiral oxazoline ligand, it exhibits excellent performance in metal-catalyzed asymmetric reactions. In the field of asymmetric catalysis, this ligand can effectively guide the chirality control of the product and improve the optical purity of the target product, which is crucial for the synthesis of fine chemicals, pharmaceutical intermediates and new materials, and has economic practicality and industrial application prospects.

[0045] It should be understood that within the scope of the present invention, the above-mentioned various technical features of the present invention and the various technical features specifically described in the following embodiments can be combined with each other to form a new or preferred technical solution. Due to space limitations, they will not be described one by one here. BRIEF DESCRIPTION OF THE DRAWINGS

[0046] The drawings of the present invention are provided for illustrative purposes only, and the proportions and quantities of the components in the drawings may not necessarily be consistent with the actual products.

[0047] Figure 1 is the NMR spectrum of target compound 1 in the embodiment of the present invention;

[0048] Figure 2 is the NMR spectrum of target compound 2 in the embodiment of the present invention;

[0049] Figure 3 It is the NMR spectrum of target compound three in the embodiment of the present invention. DETAILED DESCRIPTION

[0050] In order to make the purpose, technical solution and advantages of the embodiments of the present invention clearer, the technical solution in the embodiments of the present invention will be clearly and completely described below in conjunction with the drawings in the embodiments of the present invention. Obviously, the described embodiments are part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0051] A sulfoxide-oxazoline ligand based on a ferrocene skeleton provided in an embodiment of the present invention is a compound having the following general formula I or an enantiomer, racemate or diastereomer of the compound:

[0052]

[0053] In each formula: In each formula: R is methyl, ethyl, isopropyl, tert-butyl, benzyl, cyclohexyl, isobutyl, phenyl, p-fluorophenyl, p-tert-butylphenyl or 3,5-di-tert-butylphenyl; Ar is tolyl, p-tert-butylphenyl or p-trifluoromethylphenyl.

[0054] The compound represented by general formula I is selected from any of the following compounds:

[0055]

[0056] In each formula: R is methyl, ethyl, isopropyl, tert-butyl, benzyl, cyclohexyl, isobutyl, phenyl, p-fluorophenyl, p-tert-butylphenyl or 3,5-di-tert-butylphenyl; Ar is tolyl, p-tert-butylphenyl or p-trifluoromethylphenyl.

[0057] The compound represented by general formula I is selected from any one of target compounds 1 to 3:

[0058] Note on general reaction conditions: All reactions and controls were performed in an argon-filled glove box or using standard Schlenk techniques when air-sensitive reagents were used. Reaction solvents were dried using general standard procedures.

[0059] In an optional embodiment, the name of the target compound 1 is (4S)-tert-butyl-(2Sp)-[2-(Rs)-(p-tolylsulfoxide)ferrocenyl]-2-oxazoline, and the preparation method is:

[0060] S1: 6 g, 0.02 mol of (S)-(5-tert-butyloxazolidinediyl)ferrocene was placed in a round-bottom flask, and the flask was evacuated. Under an argon atmosphere, 4 ml, 0.024 mol of TMEDA and methyl tert-butyl ether were added; wherein the methyl tert-butyl ether was anhydrous methyl tert-butyl ether.

[0061] S2: Add 10 ml, 0.024 mol n-butyl lithium dropwise in a dry ice bath, react at -78 °C for 30 min, and react in an ice bath for 60 min;

[0062] S3: 7.07 g, 0.024 mol of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed;

[0063] S4: After the reaction is completed, water is added to quench the reaction, and ethyl acetate is added to extract the reaction mixture. The reaction mixture is dried over anhydrous sodium sulfate, dried by rotary evaporation, and purified by column chromatography with ethyl acetate and petroleum ether to obtain the target compound 1.

[0064] The target compound 1 is a yellow solid with a yield of 70%. The NMR spectrum of the target compound 1 is as follows Figure 1 As shown, NMR data:

[0065] 1 H NMR (CDCl3, 400MHz) δ = 7.83 (d, J = 7.9, 2H), 7.37 (d, J = 7.8, 2H), 4.91 (m, 1H), 4.40-4.37 (m, 1H), 4.33-4.2 8(m,1H),4.24-4.19(m,1H),4.15(m,5H),4.07-4.02(m,1H),3.97-3.95(m,1H),2.46(s,3H),2.46(s,9H).

[0066] The synthetic route is as follows:

[0067]

[0068] In another optional embodiment, the name of the target compound II is (4S)-tert-butyl-(2Rp)-[2-(Rs)-(p-tolylsulfoxide)ferrocenyl]-2-oxazoline, and the preparation method is:

[0069] S1: Put 13 g, 0.03 mol of (4S)-tert-butyl-(2Rp)-[2-(Rs)-(p-tolylsulfoxide)ferrocenyl]-2-oxazoline into a round-bottom flask, evacuate the air, and add 8 ml, 0.05 mol of TMEDA and methyl tert-butyl ether under argon atmosphere; wherein the methyl tert-butyl ether is anhydrous methyl tert-butyl ether.

[0070] S2: Add 20 ml, 0.05 mol of n-butyl lithium dropwise in a dry ice bath, react at -78 °C for 30 min, and react in an ice bath for 60 min;

[0071] S3: 15 g, 0.05 mol of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed;

[0072] S4: After the reaction is completed, water is added to quench, and ethyl acetate is added to extract, and the mixture is dried over anhydrous sodium sulfate, and then the mixture is dried by rotary evaporation and purified by ethyl acetate and petroleum ether column chromatography to obtain a yellow oil with a yield of 75%;

[0073] S5: The yellow oily product of step S4 is placed in a round-bottom flask, and the flask is ventilated. Then, 1 to 2 eq. of tetramethylammonium fluoride and dry tetrahydrofuran are added under an argon atmosphere;

[0074] S6: Stirring in an oil bath at 50°C until the reaction is complete, drying by rotary evaporation, and then purifying by ethyl acetate and petroleum ether column chromatography to obtain the target compound II;

[0075] The target compound 2 is a yellow oil with a yield of 89%. Figure 2 As shown, NMR data:

[0076] 1 H NMR (CDCl3, 400MHz) δ = 7.64 (d, J = 7.8, 2H), 7.16 (d, J = 7.8, 2H), 4.99 (m, 1H), 4.87 (m, 1H), 4.49 (m, 1 H),4.46(m,5H),4.29-4.23(m,1H),4.17-4.09(m,1H),3.97-3.91(m,1H),2.32(s,3H),0.90(s,9H).

[0077] The synthetic route is as follows:

[0078]

[0079] In another optional embodiment, the name of the target compound three is (4R)-tert-butyl-(2Rp)-[2-(Rs)-(p-tolylsulfoxide)ferrocenyl]-2-oxazoline, and the preparation method is:

[0080] S1: 6 g, 0.02 mol of (R)-(5-tert-butyloxazolidinediyl)ferrocene was placed in a round-bottom flask, and the flask was evacuated. Under argon atmosphere, 4 ml, 0.024 mol of TMEDA and methyl tert-butyl ether were added; wherein the methyl tert-butyl ether was anhydrous methyl tert-butyl ether.

[0081] S2: Add 10 ml, 0.024 mol n-butyl lithium dropwise in a dry ice bath, react at -78 °C for 30 min, and react in an ice bath for 60 min;

[0082] S3: 7.07 g, 0.024 mol of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed;

[0083] S4: After the reaction is completed, water is added to quench, and ethyl acetate is added to extract, and the mixture is dried over anhydrous sodium sulfate. After being dried by a rotary evaporator, the mixture is purified by column chromatography with ethyl acetate and petroleum ether to obtain the target compound three.

[0084] The target compound 3 is a yellow oil with a yield of 72%. The NMR spectrum of the target compound 3 is as follows Figure 3 As shown, NMR data:

[0085] 1 H NMR (CDCl3, 400MHz) δ = 7.75 (d, J = 7.9, 2H), 7.16 (d, J = 7.9, 2H), 4.98-4.96 (m, 1H), 4.76-4.7 4(m,1H),4.47-4.43(m,6H),4.27-4.17(m,2H),3.94-3.88(m,1H),2.31(s,3H),0.99(s,9H).

[0086] The synthetic route is as follows:

[0087]

[0088] The first application of sulfoxide-oxazoline ligands based on ferrocene framework:

[0089] The sulfoxide-oxazoline ligand based on the ferrocene skeleton is complexed with a metal salt of iron, gold, silver, copper, zinc, magnesium, rhodium, ruthenium, nickel, molybdenum, palladium or cobalt to prepare a catalyst.

[0090] The second use of sulfoxide-oxazoline ligands based on ferrocene skeleton:

[0091] Sulfoxide-oxazoline ligands based on ferrocene skeleton are used as catalyst ligands in metal-catalyzed coupling reactions, insertion reactions, and asymmetric reactions. Sulfoxide-oxazoline ligands based on ferrocene skeleton are used in metal-catalyzed asymmetric Friedel-Crafts alkylation reactions and asymmetric NH, OH, SH, Si-H or CH insertion reactions.

[0092] The third use of sulfoxide-oxazoline ligands based on ferrocene skeleton:

[0093] Application of sulfoxide-oxazoline ligand based on ferrocene skeleton as chiral reagent in the synthesis process of drug oseltamivir.

[0094] Synthesis of (S)-1-vinylisochroman

[0095] Weigh L1 (9.0 mg, 0.02 mmol) and Pd(OAc)2 (4.4 mg, 0.02 mmol) in a reaction flask, evacuate the air three times to make it an argon atmosphere, add 2.0 mL of xylene and stir for 30 minutes, then add 2-(2-allylphenyl)ethane-1-ol (32.4 mg, 0.20 mmol), 2,6-dimethylbenzoquinone (30 mg, 0.22 mmol) and diphenylphosphoric acid (4.4 mg, 0.02 mmol) under argon. Heat the reaction to 45 ° C until the reaction is complete and monitor by TLC. After cooling to room temperature, spin dry and column chromatography (solvent system: ethyl acetate: petroleum ether = 1:10) to obtain (S)-1-vinyl isochroman with a yield of 86%. After chiral gas chromatography analysis, the enantioselectivity of the product is 96% ee.

[0096] It should be noted that, in this article, relational terms such as first and second, etc. are only used to distinguish one entity or operation from another entity or operation, and do not necessarily require or imply any such actual relationship or order between these entities or operations. Moreover, the terms "include", "comprises" or any other variations thereof are intended to cover non-exclusive inclusion, so that a process, method, article or device that includes a series of elements includes not only those elements, but also other elements that are not explicitly listed, or also includes elements that are inherent to such process, method, article or device.

[0097] The above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit it. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that not every embodiment includes only one independent technical solution, and in the absence of a conflict of solutions, the various technical features mentioned in each embodiment can be combined in any manner to form other implementation methods that can be understood by those skilled in the art.

[0098] In addition, without departing from the scope of the present invention, the technical solutions described in the aforementioned embodiments may be modified, or some of the technical features may be replaced by equivalents, without causing the essence of the corresponding technical solutions to depart from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A sulfoxide-oxazoline ligand based on a ferrocene skeleton, which is a compound having the following general formula I or an enantiomer, racemate or diastereoisomer of the compound: In each formula: In each formula: R is methyl, ethyl, isopropyl, tert-butyl, benzyl, cyclohexyl, isobutyl, phenyl, p-fluorophenyl, p-tert-butylphenyl or 3,5-di-tert-butylphenyl; Ar is tolyl, p-tert-butylphenyl or p-trifluoromethylphenyl.

2. The sulfoxide-oxazoline ligand based on a ferrocene skeleton as claimed in claim 1, characterized in that The compound represented by general formula I is selected from any of the following compounds: In each formula: R is methyl, ethyl, isopropyl, tert-butyl, benzyl, cyclohexyl, isobutyl, phenyl, p-fluorophenyl, p-tert-butylphenyl or 3,5-di-tert-butylphenyl; Ar is tolyl, p-tert-butylphenyl or p-trifluoromethylphenyl.

3. The sulfoxide-oxazoline ligand based on a ferrocene skeleton as claimed in claim 1, characterized in that The compound represented by general formula I is selected from any one of target compounds 1 to 3:

4. The sulfoxide-oxazoline ligand based on the ferrocene skeleton as claimed in claim 3, wherein the preparation method of the target compound 1 is: S1: (S)-(5-tert-butyloxazolidinediyl)ferrocene was added with TMEDA and methyl tert-butyl ether under argon atmosphere; S2: n-Butyl lithium was added dropwise in a dry ice bath, and then reacted at -78°C for 30 min, and then in an ice bath for 60 min; S3: (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed; S4: After the reaction is completed, water is added to quench the mixture, and ethyl acetate is added to extract the mixture, followed by drying with anhydrous sodium sulfate, and then purification by column chromatography with ethyl acetate and petroleum ether to obtain the target compound 1; The synthetic route is as follows:

5. The sulfoxide-oxazoline ligand based on the ferrocene skeleton as claimed in claim 3, wherein the preparation method of the target compound 2 is: S1: (4S)-tert-butyl-(2Rp)-[2-(Rs)-(p-tolylsulfoxide)ferrocenyl]-2-oxazoline was added with TMEDA and methyl tert-butyl ether under argon atmosphere; S2: n-Butyl lithium was added dropwise in a dry ice bath, and then reacted at -78°C for 30 min, and then in an ice bath for 60 min; S3: (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed; S4: After the reaction is completed, water is added to quench, and ethyl acetate is added to extract, and the mixture is dried over anhydrous sodium sulfate, and then the mixture is dried by rotary evaporation and purified by column chromatography with ethyl acetate and petroleum ether to obtain a yellow oil; S5: The yellow oily product of step S4 is placed in a round-bottom flask, and tetramethylammonium fluoride and tetrahydrofuran are added under an argon atmosphere; S6: Stirring in an oil bath at 50°C until the reaction is complete, drying by rotary evaporation, and then purifying by ethyl acetate and petroleum ether column chromatography to obtain the target compound II; The synthetic route is as follows:

6. The sulfoxide-oxazoline ligand based on the ferrocene skeleton as claimed in claim 3, wherein the preparation method of the target compound three is: S1: (R)-(5-tert-butyloxazolidinediyl)ferrocene was added with TMEDA and methyl tert-butyl ether under argon atmosphere; S2: n-Butyl lithium was added dropwise in a dry ice bath, and then reacted at -78°C for 30 min, and then in an ice bath for 60 min; S3: (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate dissolved in anhydrous methyl tert-butyl ether was added dropwise, and the temperature was naturally raised to room temperature after the addition was completed, and the reaction was completed; S4: After the reaction is completed, water is added to quench, ethyl acetate is added to extract, and the mixture is dried over anhydrous sodium sulfate. After being dried by a rotary evaporator, the mixture is purified by column chromatography using ethyl acetate and petroleum ether to obtain the target compound three; The synthetic route is as follows:

7. Use of the sulfoxide-oxazoline ligand based on a ferrocene skeleton according to claim 1, characterized in that: The sulfoxide-oxazoline ligand based on the ferrocene skeleton is complexed with a metal salt of iron, gold, silver, copper, zinc, magnesium, rhodium, ruthenium, nickel, molybdenum, palladium or cobalt to prepare a catalyst.

8. Use of the sulfoxide-oxazoline ligand based on a ferrocene skeleton according to claim 1, characterized in that: The sulfoxide-oxazoline ligand based on the ferrocene skeleton is used as a catalyst ligand in metal-catalyzed coupling reactions, insertion reactions and asymmetric reactions.

9. The use of the sulfoxide-oxazoline ligand based on the ferrocene skeleton according to claim 8, characterized in that: The sulfoxide-oxazoline ligand based on the ferrocene skeleton is used for metal-catalyzed asymmetric Friedel-Crafts alkylation reaction and asymmetric NH, OH, SH, Si-H or CH insertion reaction.

10. Use of the sulfoxide-oxazoline ligand based on a ferrocene skeleton according to claim 1, characterized in that: The sulfoxide-oxazoline ligand based on the ferrocene skeleton is used as a chiral reagent in the synthesis process of the drug oseltamivir.

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