Chiral gamma-carbonyl phosphate derivatives, processes for their preparation and use

Abstract

The application discloses a chiral gamma-carbonyl phosphate derivative and a preparation method thereof. The method comprises the following steps: under the protection of inert gas, substrates 1 and 2 are reacted in an organic solvent and a base under the catalysis of an iridium catalyst or an iridium complex at-20-110 DEG C for 0.1-96 hours, so that the chiral gamma-carbonyl phosphate derivative is obtained, and the reaction formula is shown in the following formula. The method is simple in operation, raw materials are easy to obtain, the yield of the obtained reaction target compound is high, and the enantioselectivity is good.

Description

Technical Field

[0001] This invention relates to the field of chemical and pharmaceutical technology, and in particular to a chiral γ-carbonyl phosphate derivative and its preparation method. Background Technology

[0002] The chemistry of organophosphates has attracted considerable attention because these compounds, especially γ-carbonyl phosphates and their derivatives, which serve as important structural units, play an indispensable role in many physiological processes with vital biological activities. They are also widely used in multifunctional organic synthesis, organometallic materials, optoelectronic materials, and drugs with high chelating affinity and easy conversion to obtain highly functionalized molecules. Therefore, the synthesis of these synthetically useful scaffolds remains an important research topic.

[0003] One traditional method is the phosphorylation of alcohols with highly hazardous and air-sensitive phosphorus chloride. However, this method is cumbersome, with limitations such as a narrow substrate range, complex operation, and low synthesis efficiency, restricting the application of γ-carbonyl phosphates and their derivatives in the synthesis of natural products or drug molecules. Another method for obtaining phosphate esters is the phosphorus-Brook rearrangement reaction, which offers advantages such as high efficiency, simple operation, and high atom economy.

[0004] Developing reliable and simple methods for synthesizing enantiomeric enriched γ-carbonyl phosphates and their derivatives through asymmetric catalytic tandem reaction strategies is of great significance. However, to date, enantioselective [1,4]-phosphorus-Brook rearrangement reactions remain unexplored.

[0005] Therefore, it is necessary to develop a chiral γ-carbonyl phosphate ester and its derivatives, as well as a method for their preparation. Summary of the Invention

[0006] The purpose of this invention is to provide a chiral γ-carbonyl phosphate derivative and its preparation method. The γ-carbonyl phosphate derivative is chiral, and the method is simple to operate, the raw materials are readily available, and the resulting target compound has a high yield and good enantioselectivity.

[0007] To achieve the above objectives, the present invention adopts the following technical solution:

[0008] In a first aspect of the present invention, a chiral γ-carbonyl phosphate derivative is provided, the general structural formula of which is shown in Formula I:

[0009]

[0010] in,

[0011] R 1It is one of the following: unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, or alkyl; (the number of carbon atoms in the alkyl group ranges from 1 to 20, preferably from 1 to 8 carbon atoms).

[0012] R 2 It is one of nitro, carbonyl, sulfonyl, substituted sulfonamide, sulfinyl, substituted sulfinamide, ester (the number of carbon atoms in the ester group ranges from 1 to 20, preferably from 1 to 8), substituted amide, unsubstituted or substituted heteroaryl;

[0013] * indicates the position of the chiral carbon atom; by adjusting the ligand configuration, two products with opposite chirality can be obtained. For example, using... When used as a ligand, an optically pure product can be obtained; while using When used as a ligand, it can yield products with opposite chiral configurations.

[0014] The substituent of the substituted aryl group is one of halogen, nitro, phenolic hydroxyl, substituted sulfonamide, substituted silyl, alkyl, alkoxy, oxycarbonyl, nitrogen carbonyl, trifluoromethyl, cyano or substituted amino.

[0015] The substituent of the substituted heteroaryl group is one of halogen, nitro, phenolic hydroxyl, substituted sulfonamide, substituted silyl, alkyl, alkoxy, oxycarbonyl, nitrogen carbonyl, trifluoromethyl, cyano or substituted amino.

[0016] The substituent of the substituted sulfonamide is one of unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, or alkyl.

[0017] The substituted silicon group is one of unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, or alkyl.

[0018] The substituent of the substituted amino group is one of unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, or alkyl.

[0019] The substituents are selected from aryl, alkyl, amide, ester, sulfonyl, alkoxy, halogen, or nitro.

[0020] That is, the substituents of the aryl group are selected from alkyl, aryl, amide, ester, sulfonyl, alkoxy, halogen or nitro.

[0021] The substituents of the heteroaryl group are selected from alkyl, aryl, amide, ester, sulfonyl, alkoxy, halogen, or nitro groups.

[0022] All of the above alkyl groups have 1-20 carbon atoms.

[0023] In a second aspect of the invention, a method for preparing a chiral γ-carbonyl phosphate derivative is provided, the method comprising:

[0024] Under inert gas protection, substrate 1 and substrate 2 are reacted in an organic solvent and a base at -20 to 110 °C for 0.1 to 96 hours in the presence of an iridium catalyst or an iridium complex to obtain a chiral γ-carbonyl phosphate derivative, as shown in the following reaction formula:

[0025]

[0026] Furthermore, the base is selected from one of the following: alkali metal salts of alcohols, alkali metal salts of amines, alkali metal carbonates, alkali metal hydroxides, or organic bases.

[0027] The alkali metal salt of the alcohol is selected from one or more combinations of potassium tert-butoxide, sodium tert-butoxide, potassium isopropoxide, and sodium isopropoxide; the alkali metal salt of the amine is selected from one or more combinations of diisopropylaminolithium, bis(trimethylsilylaminolithium), bis(trimethylsilylaminosodium), and bis(trimethylsilylaminopotassium); the alkali metal carbonate is selected from one or more combinations of potassium carbonate, sodium carbonate, and cesium carbonate; the alkali metal hydroxide is selected from potassium hydroxide and / or sodium hydroxide; the organic base is triethylamine, diisopropylethylamine, tetramethylethylenediamine, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicycloundec-7-ene, 1,4-diazabicyclo[2.2.2]octane, pyridine, 4-dimethylaminopyridine, N-methylmorpholine, triethylenediamine, tetramethylguanidine, and 2-tert-butyl-1,1,3,3-tetramethylguanidine.

[0028] Preferably, the alkali is selected from organic alkalis or alkali metal carbonates. Compared with other types of alkalis, organic alkalis or alkali metal carbonates are widely available, have lower costs, are easier to use, and pose less hazard. In this system, organic alkalis or alkali metal carbonates are also easier to remove during the purification of the final product.

[0029] Further, the organic solvent is selected from at least one of methanol, ethanol, isopropanol, tert-butanol, sec-butanol, ethyl acetate, isobutyl acetate, isopropyl acetate, n-hexane, cyclohexane, n-heptane, acetone, butanone, diethyl ether, methyl tert-butyl ether, methyl cyclopentyl ether, methyl tetrahydrofuran, tetrahydrofuran, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, toluene, and dioxane.

[0030] Further, the preparation method of the iridium catalyst includes: dissolving a metallic iridium salt and a chiral ligand L in a mixed solvent of deoxygenated tetrahydrofuran and deoxygenated n-propylamine, reacting at 50±5℃ for 0.5 to 1 hour, and then evaporating the solvent under reduced pressure to obtain the iridium catalyst; preferably, the molar ratio of the metallic iridium salt and the chiral ligand L is 1:2.

[0031] The iridium catalyst prepared by this method is an active intermediate that needs to be prepared and used on-site and cannot be stored for a long time. During use, other reactants are directly added to the reaction vessel containing the iridium catalyst.

[0032] Further, the preparation method of the iridium complex includes: dissolving a metallic iridium salt and a chiral ligand L in tetrahydrofuran at 20±5℃ and reacting for 0.5 to 1 hour; then adding silver perchlorate and 4-vinyl-1,3-dioxolane-2-one and reacting at 20±5℃ for 10 to 30 hours to obtain the product; and separating the product by column chromatography to obtain the iridium complex.

[0033] Preferably, the molar ratio of the metallic iridium salt to the chiral ligand L is 1:2.

[0034] Preferably, the molar ratio of metallic iridium salt to silver perchlorate is 1:2, and the molar ratio of metallic iridium salt to 4-vinyl-1,3-dioxolane-2-one is 1:4.

[0035] The iridium complexes prepared by the above method have the advantages of being able to be prepared in advance and being able to be stored stably in air for a long time. Compared with iridium catalysts prepared on site, they can be directly added to the reaction vessel along with the reaction raw materials, which is not only more convenient to use, but also saves experimental time and improves efficiency.

[0036] The structural formula of the chiral ligand L is selected from any of the following:

[0037]

[0038] In some preferred embodiments, the chiral ligand L has the following structural formula:

[0039]

[0040] Extensive research has revealed that using either of the two ligands mentioned above results in higher yields and enantioselectivity during the preparation of γ-carbonyl phosphate derivatives.

[0041] Furthermore, the metallic iridium salt is selected from [Ir(COD)Cl]2 or [Ir(DBCOT)Cl]2;

[0042] Further, the concentration of substrate 1 is 0.001–3.0 M, the molar ratio of substrate 1 to substrate 2 is 1:2–10, and the amount of iridium catalyst or iridium complex is 0.0001–10 mol of substrate 1.

[0043] In a third aspect of the invention, the use of the chiral γ-carbonyl phosphate derivative is provided in the preparation of precursors for the synthesis of Hormosirene and (-)-dictyopterene A, wherein the precursors for the synthesis of Hormosirene and (-)-dictyopterene A are selected from... or

[0044] In a fourth aspect of the invention, the application of the chiral γ-carbonyl phosphate derivative is provided in the preparation of (R)-MCPA-CoA synthetic precursor, characterized in that the (R)-MCPA-CoA synthetic precursor is...

[0045]

[0046] In some preferred embodiments, the Hormosirene and (-)-dictyopterene A synthetic precursors are used. as well as The preparation method includes the following steps:

[0047] S1. Lithium bis(trimethylsilylamine) is added to the γ-carbonyl phosphate derivative described in one of the objectives of this invention, wherein R 1 Selected from one of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or alkyl groups; to obtain ethyl cyclopropane carboxylate derivatives, the reaction formula is as follows:

[0048]

[0049] S2. The ethyl cyclopropane formate derivative obtained in step S1 is reduced to an alcohol in the presence of lithium aluminum hydride, as shown in the following reaction formula:

[0050]

[0051] In some preferred embodiments, the preparation method of the (R)-MCPA-CCoA synthetic precursor includes the following steps:

[0052] S1. Lithium diisopropylamino is added to the γ-carbonyl phosphate derivative described in one of the objectives of this invention, wherein R 1 Selected from one of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or alkyl groups; to obtain a cyclopropylphenyl sulfone derivative, the reaction formula is as follows:

[0053]

[0054] S2. Add butyllithium to the cyclopropylphenyl sulfone derivative obtained in step S1, and add iodomethyltrimethylsilane; to obtain the substituted cyclopropylphenyl sulfone derivative, the reaction formula is as follows:

[0055]

[0056] S3. The substituted cyclopropylphenyl sulfone derivative obtained in step S2 is reduced with borane, followed by oxidation with sodium perborate to obtain the primary alcohol derivative, as shown in the following reaction formula:

[0057]

[0058] When using the γ-carbonyl phosphate derivative obtained by this invention as a raw material to prepare the above-mentioned products, compared with conventional synthesis methods, the synthesis route of this invention is shorter, the synthesis efficiency is higher, the reaction conditions are milder, the synthesis method is simpler, and the enantioselectivity of the target compound obtained is better.

[0059] Precursors for the synthesis of Hormosirene and (-)-dictyopterene A as well as (R)-MCPA-CoA synthesis precursor Conventional methods for preparing these compounds typically use chiral substrates or achieve optically pure compounds through chiral resolution. In contrast, this invention uses racemic substrates and employs asymmetric catalytic synthesis to obtain highly enantioselective products. The preparation method is simpler, faster, and yields products with higher purity.

[0060] In a fifth aspect of the invention, the use of the chiral γ-carbonyl phosphate derivative is provided in the preparation of antidepressant drugs, antitumor drugs or natural products having γ-carbonyl phosphate structural units.

[0061] The chiral γ-carbonyl phosphate derivatives described above are used to prepare the precursors for the synthesis of Hormosirene and (-)-dictyopterene A. as well as (R)-MCPA-CoA synthesis precursor This allows them to be used in the preparation of antidepressants, antitumor drugs, or natural products with γ-carbonyl phosphate structural units.

[0062] One or more technical solutions in the embodiments of the present invention have at least the following technical effects or advantages:

[0063] 1. This invention provides a chiral γ-carbonyl phosphate derivative containing multiple important functional groups, which can be easily converted into other useful groups. It can be used as a raw material to synthesize a large number of effective compounds and can also be used to prepare chiral γ-carbonyl phosphate derivatives. The derivative obtained by this invention has broad prospects for promotion and application in the preparation of antidepressants, antitumor drugs, or natural products with γ-carbonyl phosphate structural units.

[0064] 2. This invention creatively utilizes a tandem reaction of asymmetric allylation and [1,4]-phosphorus-Brook rearrangement to obtain γ-carbonyl phosphate derivatives with high stereoselectivity. Compared with conventional synthetic methods, the preparation method provided by this invention is simple to operate, low in cost, and yields high-yield and enantioselective results of the target compound, with yields of 41-91% and enantioselectivity excess >90%.

[0065] 3. The preparation method provided by this invention only requires the use of commercially available ligands. The method is simple and easy to implement and can tolerate a wide variety of substrates, including important heterocyclic substrates in medicinal chemistry. The preparation method uses iridium complexes as catalysts, which have the advantages of fast catalytic reaction rate and low catalyst dosage. Attached Figure Description

[0066] To more clearly illustrate the technical solutions in the embodiments of the present invention, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0067] Figure 1 The reaction formula is provided for the preparation method of chiral γ-carbonyl phosphate derivatives according to the embodiments of the present invention. Detailed Implementation

[0068] The present invention will be described in detail below with reference to specific embodiments and examples, thereby making the advantages and various effects of the present invention more clearly apparent. Those skilled in the art should understand that these specific embodiments and examples are for illustrative purposes only and are not intended to limit the present invention.

[0069] Throughout this specification, unless otherwise specified, the terminology used herein should be understood as having the meaning commonly used in the art. Therefore, unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. In the event of any conflict, this specification shall prevail.

[0070] Unless otherwise specified, all raw materials, reagents, instruments and equipment used in this invention can be obtained by purchasing them from the market or by existing methods.

[0071] The preparation method of a chiral γ-carbonyl phosphate derivative of this application will be described in detail below with reference to examples, comparative examples and experimental data.

[0072] The following embodiments use the chiral ligand (S,S,S)-L1 with the following structural formula: The structural formula of ligand (R,R,R)-L1 used in the following embodiments is as follows:

[0073] Example 1

[0074] Preparation

[0075] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-2-phenylethyl) dimethyl phosphonate, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 82%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralpak IF-3, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 240 nm). r =16.84 and 17.90 min; [α] 25 D = -2.5 (c 0.83, CHCl3); 1H NMR(400MHz,Chloroform-d)δ8.02-7.91(m,2H),7.60-7.53(m,1H),7.51-7.41(m,2H),5.81(ddd,J=17.5,10.4,7.2Hz,1H),5.25-5.0 3(m,2H),4.20-4.11(m,1H),4.12-4.02(m,1H),3.74(d,J=11.2Hz,3H),3.72(d,J=10.8Hz,3H),3.32-3.13(m,2H),3.12-3.02(m,1H); 13 C NMR (101MHz, Chloroform-d) δ198.1, 136.9, 136.8, 133.2, 128.6, 128.0, 117.2, 69.6 (d, J = 6.5Hz), 54.3 (d, J = 6.0Hz), 39.3 (d, J = 7.4Hz), 39.2; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 14 H 20 O5P + ([M+H)) + ):299.1043, Measured value:299.1040.

[0076] Furthermore, the reaction results using the method of Example 1 under different solvents, bases, and catalysts are shown in Table 1. Unless otherwise stated, all reactions were performed at room temperature in the presence of 5 mol% (S,S,S)-[Ir*] catalyst, with ee values ​​determined by HPLC on a chiral phase using 1 (0.2 mmol), 2a (0.4 mmol), and Cs₂CO₃ (0.2 mmol).

[0077]

[0078] Table 1

[0079]

[0080] The above results demonstrate the diversity of solvent bases and catalysts.

[0081] Example 2

[0082] Preparation

[0083] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(4-methoxyphenyl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 81%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 254 nm). r =10.58 and 12.10 min; [α] 25 D = -13.7 (c 0.90, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.99-7.89(m,2H),6.97-6.88(m,2H),5.81(ddd,J=17.4,10.4,7.1Hz,1H),5.22-5.06(m,2H),4.18- 4.10(m,1H),4.10-4.03(m,1H),3.86(s,3H),3.74(d,J=11.2Hz,3H),3.73(d,J=11.2Hz,3H),3.23-3.11(m,2H),3.07-2.96(m,1H); 13 C NMR (101MHz, Chloroform-d) δ 196.6, 163.6, 137.0, 130.3, 130.0, 117.0, 113.7, 69.7 (d, J = 6.2Hz), 55.5, 54.3 (d, J = 6.0Hz), 39.4 (d, J = 7.4Hz), 38.8; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 15 H 22 O6P + ([M+H)) +):329.1149, Measured value:329.1152.

[0084] Example 3

[0085] Preparation

[0086] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(4-bromophenyl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 91%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 94% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 254 nm). r =9.22 and 10.55 min; [α] 15 D = -12.1 (c 1.00, CH2Cl2); 1 H NMR(400MHz,Chloroform-d)δ7.85-7.77(m,2H),7.65-7.55(m,2H),5.79(ddd,J=17.6,10.5,7.3Hz,1H),5.22-5.04(m,2H), 4.18-4.09(m,1H),4.09-4.00(m,1H),3.73(d,J=11.2Hz,3H),3.72(d,J=11.2Hz,3H),3.26-3.10(m,2H),3.08-2.96(m,1H); 13 C NMR (101MHz, Chloroform-d) δ197.1, 136.6, 135.6, 131.9, 129.5, 128.4, 117.3, 69.5 (d, J = 6.0Hz), 54.3 (d, J = 6.0Hz), 39.3 (d, J = 7.5Hz), 39.1; 31P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 14 H 19 BrO5P + ([M+H)) + ):377.0148, Measured value:377.0145.

[0087] Example 4

[0088] Preparation

[0089] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-2-(p-tolyl)ethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 85%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 98% excess (Chiralcel OD-H, i-propanol / hexane = 10 / 90, flow rate 1.0 mL / min, λ = 254 nm); t r =14.35 and 15.77 min; [α] 25 D = -5.7 (c 1.05, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.89-7.81(m,2H),7.26-7.21(m,2H),5.81(ddd,J=17.5,10.4,7.3Hz,1H),5.23-5.05(m,2H),4.18- 4.10(m,1H),4.10-4.02(m,1H),3.74(d,J=10.8Hz,3H),3.72(d,J=11.2Hz,3H),3.27-3.13(m,2H),3.11-2.97(m,1H),2.40(s,3H); 13C NMR (101MHz, Chloroform-d) δ197.8, 144.0, 136.9, 134.4, 129.3, 128.2, 117.1, 69.7 (d, J = 6.0Hz), 54.3 (d, J = 5.9Hz), 39.4 (d, J = 7.5Hz), 39.1, 21.6; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 15 H 22 O5P + ([M+H)) + ):313.1200, Measured value:313.1194.

[0090] Example 5

[0091] Preparation

[0092] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 74%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 94% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 220 nm). r =7.94 and 9.05 min; [α] 25 D = -1.0 (c 0.52, CHCl3); 1H NMR(400MHz,Chloroform-d)δ8.14-8.01(m,2H),7.77-7.68(m,2H),5.80(ddd,J=17.6,10.4,7.4Hz,1H),5.23-5.08(m,2H),4.20-4.12(m,1H),4 .10-4.03(m,1H),3.74(d,J=11.2Hz,3H),3.73(d,J=11.2Hz,3H),3.27(dd,J=16.5,5.6Hz,1H),3.23-3.13(m,1H),3.08(dd,J=16.6,6.9Hz,1H); 13 C NMR(101MHz,Chloroform-d)δ197.2,139.5,136.4,134.4(q,J=32.5Hz),128.4,125.7(q,J=3.8H z), 123.5 (q, J = 272.7Hz), 117.5, 69.5 (d, J = 5.9Hz), 54.3 (d, J = 5.9Hz), 39.5, 39.2 (d, J = 7.3Hz); 19 F NMR(376MHz,Chloroform-d)δ-63.1; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 15 H 19 F3O5P + ([M+H)) + ):367.0917, Measured value:367.0906.

[0093] Example 6

[0094] Preparation

[0095] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(3-methoxyphenyl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 75%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 97% excess (Chiralpak AS-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 220 nm). r =20.96 and 24.27 min; [α] 25 D = -3.8 (c 0.93, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.55-7.51(m,1H),7.47(dd,J=2.7,1.6Hz,1H),7 .36(dd,J=8.0,8.0Hz,1H),7.14-7.08(m,1H),5.81(ddd,J=17.5,10.4,7.3Hz,1 H),5.22-5.08(m,2H),4.19-4.10(m,1H),4.10-4.01(m,1H),3.85(s,3H),3.74( d,J=11.2Hz,3H),3.73(d,J=11.2Hz,3H),3.28-3.12(m,2H),3.11-3.00(m,1H); 13 C NMR(101MHz,Chloroform-d)δ198.0,159.8,138.3,136.8,129.6,120.7,119.7,1 17.2, 112.3, 69.6 (d, J = 6.2Hz), 55.4, 54.3 (d, J = 6.0Hz), 39.4 (d, J = 7.4Hz), 39.3; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 15 H 22O6P + ([M+H)) + ):329.1149, Measured value:329.1143.

[0096] Example 7

[0097] Preparation

[0098] Add 0.005 mmol [Ir(COD)Cl] to a 25 mL reaction tube. 2 0.010 mmol (S,S,S)-L1, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were reacted at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(3-chlorotoluene)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 69%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 90% excess (Chiralpak AS-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 210 nm). r =17.22 and 20.00 min; [α] 25 D = -0.4 (c 0.53, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.92-7.89(m,1H),7.84-7.79(m,1H),7.55-7.50(m,1H),7.43-7.36(m,1H),5.79(ddd,J=17.5,10.4,7.3Hz,1H), 5.22-5.08(m,2H),4.18-4.10(m,1H),4.09-4.01(m,1H),3.74(d,J=11. 2Hz,3H),3.73(d,J=11.2Hz,3H),3.26-3.11(m,2H),3.09-2.98(m,1H); 13C NMR(101MHz,Chloroform-d)δ196.8,138.4,136.5,135.0,133.1,130.0,128.1 ,126.1,117.4,69.5(d,J=6.4Hz),54.4(d,J=6.0Hz),39.3,39.2(d,J=7.4Hz); 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 14 H 19 ClO5P + ([M+H)) + ):333.0654, Measured value:333.0651.

[0099] Example 8

[0100] Preparation

[0101] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(m-toluene)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 70%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralpak IE, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 210 nm). r =24.09 and 25.59 min; [α] 25 D = -6.6(c 0.69,acetone); 1H NMR(400MHz,Chloroform-d)δ7.78-7.71(m,2H),7.41-7.30(m,2H),5.81(ddd,J=17.6,10.4,7.3Hz,1H),5.24-5.07(m,2H),4.19- 4.11(m,1H),4.10-4.02(m,1H),3.74(d,J=10.8Hz,3H),3.73(d,J=10.8Hz,3H),3.29-3.13(m,2H),3.12-2.99(m,1H),2.40(s,3H); 13 C NMR(101MHz,Chloroform-d)δ198.3,138.4,136.9,136.9,134.0,128.5,128.5,1 25.2,117.1,69.6(d,J=6.0Hz),54.3(d,J=5.9Hz),39.3(d,J=7.4Hz),39.2,21.3; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 15 H 22 O5P + ([M+H)) + ):313.1200, Measured value:313.1198.

[0102] Example 9

[0103] Preparation

[0104] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(2-methoxyphenyl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 62%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 246 nm). r =8.65 and 9.69 min; [α] 25 D = -16.3 (c 0.79, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.65(dd,J=7.7,1.9Hz,1H),7.48-7.41(m,1H),7.03-6.92(m,2H),5.78(ddd,J=17.5,10.4,7.2Hz,1H),5.19-5.05( m,2H),4.12-4.06(m,1H),4.06-3.99(m,1H),3.89(s,3H),3.732(d,J=11 .2Hz,3H),3.728(d,J=11.2Hz,3H),3.27-3.16(m,1H),3.16-3.01(m,2H); 13 C NMR(101MHz,Chloroform-d)δ200.4,158.4,137.2,133.5,130.3,128.2,120.7,1 16.8, 111.4, 69.8 (d, J = 6.4Hz), 55.4, 54.2 (d, J = 5.9Hz), 44.5, 39.6 (d, J = 7.4Hz); 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 15 H 22 O6P +([M+H)) + ):329.1149, Measured value:329.1148.

[0105] Example 10

[0106] Preparation

[0107] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(2-chlorophenyl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 84%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 96% excess (Chiralcel OD-H, i-propanol / hexane = 10 / 90, flow rate 1.0 mL / min, λ = 210 nm). r =14.88 and 16.65 min; [α] 25 D = -1.7 (c 1.02, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.49-7.43(m,1H),7.42-7.34(m,2H),7.34-7.28(m,1H),5.77(ddd,J=17.5,10.4,7.3Hz,1H),5.22-5.09(m,2H) ,4.16-4.08(m,1H),4.07-4.00(m,1H),3.74(d,J=11.1Hz,6H),3.22(dd,J=16.3,5.3Hz,1H),3.18-3.09(m,1H),3.05(dd,J=16.2,7.1Hz,1H); 13C NMR(101MHz,Chloroform-d)δ201.2,139.2,136.4,131.8,130.8,130.5,129.0 ,127.0,117.5,69.4(d,J=6.0Hz),54.3(d,J=5.7Hz),43.7,39.6(d,J=8.0Hz); 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 14 H 19 ClO5P + ([M+H)) + ):333.0654, Measured value:333.0651.

[0108] Example 11

[0109] Preparation

[0110] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(o-tolyl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 72%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 95% excess (Chiralpak AD-H, i-propanol / hexane = 5 / 95, flow rate 0.7 mL / min, λ = 210 nm). r =31.14 and 33.37 min; [α] 25 D = -5.3 (c 0.88, CHCl3); 1H NMR(400MHz,Chloroform-d)δ7.67-7.58(m,1H),7.40-7.33(m,1H),7.26-7.21(m,2H),5.79(ddd,J=17.5,10.5,7.3Hz,1H),5.23-5.07(m,2H) ),4.17-4.09(m,1H),4.08-4.00(m,1H),3.744(d,J=11.2Hz,3H),3.74 1(d,J=10.8Hz,3H),3.21-3.08(m,2H),3.04-2.92(m,1H),2.47(s,3H); 13 C NMR(101MHz,Chloroform-d)δ202.2,138.1,137.9,136.8,132.0,131.4,128.4,1 25.7, 117.2, 69.6 (d, J = 5.9Hz), 54.3 (d, J = 6.0Hz), 42.2, 39.6 (d, J = 7.4Hz), 21.1; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 15 H 22 O5P + ([M+H)) + ):313.1200, Measured value:313.1198.

[0111] Example 12

[0112] Preparation

[0113] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(naphthyl-1-yl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 74%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 96% excess (Chiralpak AD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 210 nm). r =8.23 and 8.90 min; [α] 25 D = -4.3 (c 0.80, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ8.54(dd,J=8.5,1.3Hz,1H),8.02-7.94(m,1H),7.90-7 .82(m,2H),7.61-7.46(m,3H),5.84(ddd,J=17.5,10.4,7.4Hz,1H),5.23-5.11(m,2H ),4.23-4.14(m,1H),4.14-4.08(m,1H),3.734(d,J=11.2Hz,3H),3.726(d,J=10.8Hz ,3H),3.34(dd,J=16.1,5.6Hz,1H),3.30-3.19(m,1H),3.14(dd,J=16.1,7.3Hz,1H); 13 C NMR(101MHz,Chloroform-d)δ202.3,136.6,135.9,133.9,132.7,130.0,128.4,127.9,127.5 ,126.5,125.6,124.3,117.4,69.6(d,J=6.0Hz),54.3(d,J=5.9Hz),42.7,39.8(d,J=7.4Hz); 31P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 18 H 22 O5P + ([M+H)) + ):349.1200, Measured value:349.1198.

[0114] Example 13

[0115] Preparation

[0116] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(naphthyl-2-yl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 77%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralpak IF-3, i-propanol / hexane = 10 / 90, flow rate 1.0 mL / min, λ = 240 nm). r =31.66 and 33.12 min; [α] 25 D = -6.7 (c 0.95, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ8.54-8.43(m,1H),8.05-7.94(m,2H),7.92-7.84(m,2H),7.64-7.51(m,2H),5.86(ddd,J=17.4,10.4,7.2Hz,1H), 5.25-5.10(m,2H),4.24-4.16(m,1H),4.16-4.08(m,1H),3.74(d,J=10. 8Hz,3H),3.73(d,J=11.2Hz,3H),3.44-3.32(m,1H),3.30-3.14(m,2H); 13C NMR(101MHz,Chloroform-d)δ198.0,136.8,135.6,134.2,132.4,129.8,129.5,128.52,128.4 9,127.7,126.8,123.7,117.2,69.7(d,J=6.0Hz),54.3(d,J=6.4Hz),39.5(d,J=7.4Hz),39.2; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 18 H 22 O5P + ([M+H)) + ):349.1200, Measured value:349.1204.

[0117] Example 14

[0118] Preparation

[0119] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(pyridin-2-yl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 67%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be >99% (Chiralpak AS-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 230 nm); t r =18.37 and 26.93 min; [α] 25 D = -3.0 (c 0.55, CHCl3); 1H NMR(400MHz,Chloroform-d)δ8.70-8.63(m,1H),8.08-7.96(m,1H),7.86-7.78(m,1H),7.49-7.43(m,1H),5.80(ddd,J=17.6,10.4,7.5Hz,1H),5 .22-5.04(m,2H),4.18-4.10(m,1H),4.10-4.02(m,1H),3.731(d,J=11. 2Hz,3H),3.727(d,J=10.8Hz,3H),3.45-3.35(m,2H),3.25-3.14(m,1H); 13 C NMR (101MHz, Chloroform-d) δ 199.8, 153.2, 148.9, 137.0, 136.9, 127.2, 121.8, 117.1, 69.7 (d, J = 5.9Hz), 54.3 (d, J = 6.2Hz), 39.4 (d, J = 7.6Hz), 38.4; 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 13 H 19 NO5P + ([M+H)) + ):300.0996, Measured value:300.0999.

[0120] Example 15

[0121] Preparation

[0122] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(thiophene-2-yl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 75%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 94% excess (Chiralpak AD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 254 nm). r =8.63 and 9.73 min; [α] 25 D = -2.2 (c 0.77, CHCl3); 1 H NMR (400MHz, Chloroform-d) δ7.72(dd,J=3.8,1.1Hz,1H),7.64(dd,J=4.9,1.1Hz,1H),7.13(dd,J=5.0,3.8Hz,1H),5.80(ddd,J=17.4,10.4,7.2Hz, 1H),5.21-5.09(m,2H),4.19-4.10(m,1H),4.09-4.03(m,1H),3.74(d,J=1 1.2Hz,3H),3.72(d,J=10.8Hz,3H),3.24-3.10(m,2H),3.06-2.95(m,1H); 13 C NMR (101MHz, Chloroform-d) δ191.0, 144.3, 136.5, 133.9, 132.0, 128.1, 117.4, 69.5 (d, J = 6.0Hz), 54.3 (d, J = 6.3Hz), 40.0, 39.7 (d, J = 7.4Hz); 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 12 H 18 O5PS + ([M+H)) +):305.0608, Measured value:305.0610.

[0123] Example 16

[0124] Preparation

[0125] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-(furan-2-yl)-2-oxoethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 71%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 93% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 270 nm). r =8.63 and 9.73 min; [α] 25 D =0.2 (c 0.59, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.57(dd,J=1.7,0.8Hz,1H),7.19(dd,J=3.6,0.8Hz,1 H),6.53(dd,J=3.6,1.7Hz,1H),5.77(ddd,J=18.0,10.4,7.2Hz,1H),5.21-5.05(m,2 H),4.15-4.07(m,1H),4.07-4.00(m,1H),3.74(d,J=11.2Hz,3H),3.72(d,J=11.2Hz ,3H),3.20-3.09(m,1H),3.04(dd,J=16.3,6.1Hz,1H),2.94(dd,J=16.3,7.5Hz,1H); 13C NMR (101MHz, Chloroform-d) δ 187.2, 152.7, 146.5, 136.4, 117.4, 117.3, 112.3, 69.5 (d, J = 6.1Hz), 54.3 (d, J = 6.3Hz), 39.4 (d, J = 7.7Hz), 39.1; 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 12 H 18 O6P + ([M+H)) + ):289.0836, Measured value:289.0833.

[0126] Example 17

[0127] Preparation

[0128] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxopropyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 58%. The enantioselectivity of the product was determined by the derivative obtained from the olefin metathesis reaction of the product with styrene. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (HPLC) and found to be 96% excess (Chiralcel OJ-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 252 nm). r =16.59 and 19.60 min; [α] 25 D =8.0 (c0.55, CHCl3); 1H NMR(400MHz,Chloroform-d)δ5.71(ddd,J=17.7,10.5,7.6Hz,1H),5.18-5.05(m,2H),4.08-4.00(m,1H),3.98-3.90(m, 1H),3.74(d,J=10.8Hz,6H),3.02-2.90(m,1H),2.67(dd,J=17.1,6.1Hz,1H),2.51(dd,J=17.1,7.4Hz,1H),2.14(s,3H); 13 C NMR (101MHz, Chloroform-d) δ206.8, 136.5, 117.2, 69.4 (d, J = 5.9Hz), 54.4 (d, J = 6.0Hz), 44.1, 39.0 (d, J = 7.4Hz), 30.5; 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated C9H 18 O5P + ([M+H)) + ):237.0887, Measured value:237.0886.

[0129] Example 18

[0130] Preparation

[0131] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-cyclopropyl-2-oxoethyl) dimethyl phosphonate, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 59%. The enantioselectivity of the product was determined by the derivative obtained from the olefin metathesis reaction of the product with styrene. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (HPLC) and found to be 98% excess (Chiralpak AS-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 252 nm). r=20.49 and 22.72 min; [α] 25 D =2.5 (c 0.63, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.73(ddd,J=17.6,10.4,7.5Hz,1H),5.18-5.06(m,2H),4.08-4.00(m,1H),4.00-3.93(m,1H),3.75(d,J=10.8Hz ,6H),3.06-2.93(m,1H),2.80(dd,J=16.8,6.1Hz,1H),2.64(dd,J=16.8,7.5Hz,1H),1.95-1.89(m,1H),1.04-0.97(m,2H),0.90-0.82(m,2H); 13 C NMR (101MHz, Chloroform-d) δ208.8, 136.7, 117.1, 69.5 (d, J = 6.0Hz), 54.3 (d, J = 5.9Hz), 44.0, 39.1 (d, J = 7.5Hz), 20.9, 10.90, 10.85; 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 11 H 20 O5P + ([M+H)) + ):263.1043, Measured value:263.1042.

[0132] Example 19

[0133] Preparation

[0134] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-cyclohexyl-2-oxoethyl) dimethyl phosphonate, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 44%. The enantioselectivity of the product was determined by the derivative obtained from the olefin metathesis reaction of the product with styrene. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (HPLC) and found to be 97% excess (Chiralpak AS-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 252 nm). r =11.97 and 15.76 min; [α] 25 D =3.6 (c 0.40, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.71(ddd,J=17.7,10.4,7.6Hz,1H),5.15-5.05(m,2H),4.06-3.99(m,1H),3.98-3.90(m,1H),3.74(d,J=11.2Hz ,6H),3.04-2.92(m,1H),2.65(dd,J=17.3,6.1Hz,1H),2.54(dd,J=17.3,7.3Hz,1H),2.36-2.25(m,1H),1.83-1.72(m,4H),1.36-1.13(m,6H); 13 C NMR (101MHz, Chloroform-d) δ211.9,136.9,116.9,69.5(d,J=6.0Hz),54.3(d,J=6.0Hz),51.1,41.2,38.8(d,J=7.5Hz),28.3,28.2,25.7,25.6,25.5; 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 14 H 26 O5P+ ([M+H)) + ):305.1513, measured value:305.1151.

[0135] Example 20

[0136] Preparation

[0137] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-2-phenylethyl) phosphonate diethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 72%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 98% excess (Chiralpak AS-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 240 nm). r =9.52 and 10.66 min; [α] 25 D = -7.2 (c 0.50, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.99-7.91(m,2H),7.60-7.53(m,1H),7.50-7.42(m,2H),5.82(ddd,J=17.5,10.4,7.3Hz,1H),5.19- 5.06(m,2H),4.16-4.03(m,6H),3.25(dd,J=16.6,5.7Hz,1H),3.23-3.13(m,1H),3.06(dd,J=16.3,6.8Hz,1H),1.33-1.27(m,6H); 13C NMR (101MHz, Chloroform-d) δ198.2, 136.9, 133.2, 128.6, 128.0, 117.0, 69.3 (d, J = 6.1Hz), 63.8 (d, J = 6.0Hz), 39.3 (d, J = 7.3Hz), 39.2, 16.1 (d, J = 6.7Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻¹.0; HRMS (ESI+) calculated value C 16 H 24 O5P + ([M+H)) + ):327.1356, Measured value:327.1351.

[0138] Example 21

[0139] Preparation

[0140] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-2-phenylethyl)phosphonate diisopropyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 61%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 97% excess (Chiralpak AS-H, i-propanol / hexane = 10 / 90, flow rate 1.0 mL / min, λ = 240 nm). r =11.87 and 13.51 min; [α] 25 D =4.0 (c 0.40, CHCl3); 1H NMR(400MHz,Chloroform-d)δ7.98-7.90(m,2H),7.58-7.52(m,1H),7.49-7.41(m,2H),5.81(ddd,J=17.6,10.4,7.5Hz,1H),5.19-5.06(m,2H),4.67- 4.51(m,2H),4.14-4.06(m,1H),4.05-3.97(m,1H),3.25(dd,J=16.5,5.6Hz ,1H),3.21-3.10(m,1H),3.04(dd,J=16.5,7.1Hz,1H),1.31-1.26(m,12H); 13 C NMR(101MHz,Chloroform-d)δ198.2,137.0,136.9,133.1,128.6,128.0,116.9,72.4(d,J=6 .0Hz), 69.1 (d, J = 6.4Hz), 39.32 (d, J = 8.0Hz), 39.30, 23.6 (d, J = 4.3Hz), 23.5 (d, J = 3.8Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻².⁸; HRMS (ESI+) calculated value C 18 H 28 O5P + ([M+H)) + ):355.1669, Measured value:355.1665.

[0141] Example 22

[0142] Preparation

[0143] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metallic iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-2-phenylethyl)phosphonate dibenzyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 79%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralcel OJ-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 210 nm). r =16.04 and 19.51 min; [α] 25 D =2.4 (c 0.61, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.93-7.87(m,2H),7.58-7.52(m,1H),7.48-7.40(m,2H),7.38-7.28(m,10H),5.74(ddd,J=17.5,10 .4,7.3Hz,1H),5.15-5.06(m,2H),5.06-4.96(m,4H),4.12-4.05(m,1H),4.04-3.97(m,1H),3.18-3.07(m,2H),3.03-2.92(m,1H); 13 C NMR(101MHz,Chloroform-d)δ198.0,136.9,136.7,135.8(d,J=6.6Hz),133.1,128.6,128.5, 128.5, 128.0, 127.9, 117.1, 69.6 (d, J = 6.1Hz), 69.3 (d, J = 5.4Hz), 39.17, 39.16 (d, J = 7.9Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻⁹; HRMS (ESI+) calculated value C 26 H 28 O5P + ([M+H)) +):451.1669, measured value:451.1670.

[0144] Example 23

[0145] Preparation

[0146] In a 25 mL reaction tube, 0.005 mmol [Ir(COD)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol of 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)ethyl acetate, 0.4 mmol of 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol of cesium carbonate, and 2 mL of tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography in 66% yield. The enantioselectivity of the product was determined by subsequent transformation example 23; [α] 25 D =2.7(c0.7,CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.71(ddd,J=17.2,10.5,7.7Hz,1H),5.22-5.14(m,2H),4.42-4.33(m,4H),4.19-4 .08(m,4H),3.01-2.90(m,1H),2.51(dd,J=15.7,6.5Hz,1H),2.41(dd,J=15.8,7.4Hz,1H),1.24(t,J=7.1Hz,3H); 13 C NMR(101MHz,Chloroform-d)δ171.4,135.5,122.2(qd,J=278.7,9.7Hz),118.0,7 0.7(d,J=6.0Hz),63.9(qd,J=38.4,4.6Hz),60.7,40.2(d,J=7.7Hz),35.4,14.1; 31 P NMR (162MHz, Chloroform-d) δ-2.6; HRMS (ESI+) calculated value C 12 H 18 F6O6P + ([M+H)) +):403.0740, Measured value:403.0750.

[0147] Example 24

[0148] Preparation

[0149] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (nitromethyl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 80%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 210 nm). r =13.99 and 15.80 min; [α] 25 D =19.2 (c 0.53, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.71(ddd,J=17.4,10.2,7.9Hz,1H),5.33-5.25(m,2H),4.61(dd,J=12.7,6.1Hz,1H ),4.45(dd,J=12.7,7.9Hz,1H),4.20-4.13(m,1H),4.09-4.00(m,1H),3.78(d,J=10.8Hz,6H),3.34-3.22(m,1H); 13 CNMR(101MHz,Chloroform-d)δ131.7,120.5,66.9(d,J=5.6Hz),54.6(d,J=5.9Hz),42.5(d,J=7.4Hz); 31 P NMR (162MHz, Chloroform-d) δ 0.9; HRMS (ESI+) calculated C7H 15 NO6P + ([M+H))+ ):240.0632, Measured value:240.0627.

[0150] Example 25

[0151] Preparation

[0152] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol ((phenylsulfonyl)methyl)phosphonate diethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 67%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 97% excess (Chiralpak IA, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 216 nm). r =10.73 and 12.49 min; [α] 25 D =4.2 (c 0.57, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.94-7.83(m,2H),7.68-7.61(m,1H),7.59-7.50(m,2H),5.68(ddd,J=17.2,10.2,7.9Hz,1H),5.18-5.08(m,2H),4 .18-4.03(m,5H),3.99(dt,J=10.1,6.1Hz,1H),3.39(dd,J=14.3,5.5Hz, 1H),3.15(dd,J=14.2,7.4Hz,1H),3.06-2.95(m,1H),1.34-1.27(m,6H); 13C NMR (101MHz, Chloroform-d) δ139.5, 134.7, 133.8, 129.3, 128.0, 118.6, 68.4 (d, J = 5.8Hz), 64.0 (d, J = 5.7Hz), 56.6, 39.0 (d, J = 7.8Hz), 16.1 (d, J = 6.9Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻¹.3; HRMS (ESI+) calculated value C 15 H 24 O6PS + ([M+H)) + ):363.1026, Measured value:363.1020.

[0153] Example 26

[0154] Preparation

[0155] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (cyanomethyl)phosphonate diethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 68%. The enantioselectivity of the product was determined by the derivative obtained from the olefin metathesis reaction of the product with styrene. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (HPLC) and found to be 94% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 252 nm). r =13.06 and 16.31 min; [α] 25 D =5.4 (c 0.4, CHCl3); 1H NMR(400MHz,Chloroform-d)δ5.71(ddd,J=17.7,10.3,7.7Hz,1H),5.37-5.18(m,2H),4.18-4.03(m,5H),4.00- 3.90(m,1H),2.84-2.71(m,1H),2.59(dd,J=16.8,5.5Hz,1H),2.51(dd,J=16.8,7.2Hz,1H),1.36-1.27(m,6H); 13 C NMR (101MHz, Chloroform-d) δ133.6, 119.4, 117.5, 67.7 (d, J = 5.9Hz), 64.0 (d, J = 6.0Hz), 40.3 (d, J = 7.4Hz), 19.3, 16.0 (d, J = 6.7Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻¹.3; HRMS (ESI+) calculated value C 10 H 19 NO4P + ([M+H)) + ):248.1047, Measured value:248.1048.

[0156] Example 27

[0157] Preparation

[0158] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (pyrimidin-4-ylmethyl)phosphonate diethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 71%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography (Chiralpak IF-3, i-propanol / hexane = 15 / 85, flow rate 1.0 mL / min, λ = 246 nm). r =21.72 and 22.64 min; [α]25 D =6.2 (c 0.42, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ9.13(d,J=1.4Hz,1H),8.61(d,J=5.2Hz,1H),7.19(dd,J=5.2,1.4Hz,1H),5.71(ddd,J=17.2,10.5 ,7.8Hz,1H),5.12-4.98(m,2H),4.15-4.07(m,4H),4.06-3.98(m,2H),3.08-2.99(m,2H),2.86-2.76(m,1H),1.35-1.31(m,6H); 13 C NMR(101MHz,Chloroform-d)δ168.0,158.6,156.6,136.3,121.5,117.9,69.3(d,J=7.3 6z), 63.8 (d, J = 5.9Hz), 43.3 (d, J = 7.5Hz), 38.8, 16.1 (d, J = 6.7Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻¹.1; HRMS (ESI+) calculated value C 13 H 22 N2O4P + ([M+H)) + ):301.1312, Measured value:302.1311.

[0159] Example 28

[0160] Preparation

[0161] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxolane-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (benzo[d]thiazol-4-ylmethyl)phosphonate diethyl ester, 0.4 mmol 4-vinyl-1,3-dioxolane-2-one, 0.20 mmol cesium carbonate, and 2 mL tetrahydrofuran were added sequentially, and the reaction was carried out at 50 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 62%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 98% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 220 nm). r =5.50 and 6.24 min; [α] 25 D =4.2 (c 1.49, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.96(dd,J=8.4,1.2Hz,1H),7.83(dd,J=8.0,1.2Hz,1H),7.49-7.42(m,1H),7.39-7.32(m,1H),5.81(ddd,J=17.3,10.4 ,7.8Hz,1H),5.23-5.07(m,2H),4.19-4.02(m,6H),3.38(dd,J=14.7,5.9H z,1H),3.19(dd,J=14.7,8.3Hz,1H),3.15-3.03(m,1H),1.36-1.27(m,6H); 13 C NMR(101MHz,Chloroform-d)δ168.9,153.1,136.1,135.2,125.9,124.8,122.6,121.5,1 18.2, 69.1 (d, J = 6.1Hz), 63.9 (d, J = 5.9Hz), 44.1 (d, J = 7.6Hz), 35.4, 16.1 (d, J = 7.1Hz); 31 P NMR (162MHz, Chloroform-d) δ⁻¹.1; HRMS (ESI+) calculated value C 16 H 23 NO4PS+ ([M+H)) + ):356.1080, Measured value:356.1080.

[0162] Example 29

[0163] Preparation

[0164] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]2, 0.010 mmol (S,S,S)-L1, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (E)-(2-oxo-4-phenylbut-3-en-1-yl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 74%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 97% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 284 nm). r =14.19 and 27.38 min; [α] 25 D = -7.1 (c 0.88, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ7.60-7.51(m,3H),7.43-7.34(m,3H),6.73(d,J= 16.2Hz,1H),5.78(ddd,J=17.6,10.4,7.5Hz,1H),5.23-5.07(m,2H),4.15-4.0 7(m,1H),4.07-4.00(m,1H),3.753(d,J=10.4Hz,3H),3.751(d,J=10.8Hz,3H), 3.18-3.03(m,1H),2.92(dd,J=16.6,6.1Hz,1H),2.77(dd,J=16.6,7.4Hz,1H); 13C NMR(101MHz,Chloroform-d)δ198.0,143.0,136.7,134.3,130.6,128.9,128.3 ,126.1,117.2,69.6(d,J=6.4Hz),54.3(d,J=5.9Hz),41.4,39.4(d,J=7.4Hz); 31 P NMR (162MHz, Chloroform-d) δ1.2; HRMS (ESI+) calculated value C 16 H 22 O5P + ([M+H)) + ):325.1200, Measured value:325.1199.

[0165] Example 30

[0166] Preparation

[0167] In a 25 mL reaction tube, 0.005 mmol [Ir(DBCOT)Cl]₂, 0.010 mmol (S,S,S)-L₁, 0.5 mL deoxygenated THF, and 0.5 mL deoxygenated n-propylamine were added. The reaction was carried out at 50 °C for 30 minutes, and the solvent was evaporated under reduced pressure to obtain the iridium catalyst (or an iridium complex was prepared using a metal iridium salt and a chiral ligand, silver perchlorate, and 4-vinyl-1,3-dioxocyclopentan-2-one, with the amount of iridium complex being 0.01 mmol). Under nitrogen protection at 25 °C, 0.20 mmol (2-oxo-4-phenylbut-3-yn-1-yl)phosphonate dimethyl ester, 0.4 mmol 4-vinyl-1,3-dioxocyclopentan-2-one, 0.20 mmol cesium carbonate, and 2 mL dichloromethane were added sequentially, and the reaction was carried out at 25 °C. The reaction was monitored by thin-layer chromatography. After the reaction was completed, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography with a yield of 72%. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 91% excess (Chiralpak IB, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 270 nm). r =10.75 and 27.28 min; [α] 25 D = -2.5 (c 0.79, CHCl3); 1H NMR(400MHz,Chloroform-d)δ7.61-7.54(m,2H),7.50-7.43(m,1H),7.42-7.35(m,2H),5.77(ddd,J=17.2,10.4,7.5Hz,1H),5.27-5.13(m,2H) ,4.15-4.07(m,1H),4.06-3.97(m,1H),3.77(d,J=11.1Hz,6H),3.22-3.10(m,1H),2.94(dd,J=16.7,5.9Hz,1H),2.78(dd,J=16.6,7.8Hz,1H); 13 C NMR (101MHz, Chloroform-d) δ185.5,135.9,133.1,130.9,128.6,119.7,117.8,91.3,87.8,69.3(d,J=6.1Hz),54.4(d,J=5.9Hz),46.2,39.6(d,J=7.5Hz); 31 P NMR (162MHz, Chloroform-d) δ1.1; HRMS (ESI+) calculated value C 16 H 19 NaO5P + ([M+Na)) + ):345.0863, Measured value:345.0854.

[0168] Example 31

[0169] Preparation

[0170] The flame-dried Schlenk tube was cooled to room temperature and filled with N2. The product of Example 23 (402.2 mg, 1.0 mmol) and THF (2.0 mL) were added to the flask. The reaction mixture was cooled to -78 °C, and freshly prepared LiHMDS (1.0 M in THF, 2.0 equiv) was added dropwise. The reaction mixture was brought to room temperature and stirred until the starting material was completely consumed (detected by TLC). The reaction mixture was cooled to 0 °C and treated with a saturated aqueous ammonium chloride solution. The organic phase was separated, and the aqueous phase was extracted three times with Et2O. The combined organic phases were dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give the product in 88% yield, with an enantioselectivity of 94% as determined by chiral gas chromatography (BetaDEX-120, N2 flow rate 1.0 mL / min, 2 min at 70 °C, then 0.1 °C·min). -1 (to 75℃); t r=24.38 and 24.93 min; [α] 25 D =75.6 (c 0.77, CHCl3); 1 H NMR (400MHz, Chloroform-d) δ5.39(ddd,J=17.0,10.2,8.4Hz,1H),5.16(dd,J=17.1,1.2Hz,1H),4.99(dd,J=10.2,1.5Hz,1H),4.13(q,J=7.1Hz,2H),2.01( tdd,J=8.7,6.2,4.0Hz,1H),1.63(ddd,J=8.4,5.2,4.0Hz,1H),1.36(ddd,J=8 .9,5.2,4.4Hz,1H),1.26(t,J=7.1Hz,3H),0.97(ddd,J=8.4,6.2,4.3Hz,1H); 13 C10 NMR (101 MHz, Chloroform-d) δ 173.4, 138.1, 114.8, 60.6, 25.5, 21.8, 15.5, 14.2; HRMS (ESI+) calculated C8H 13 O2 + ([M+H)) + ):141.0911, Measured value:141.0909.

[0171] Example 32

[0172] Preparation

[0173] The flame-dried Schlenk tube was cooled to room temperature. LiAlH4 (19.0 mg, 0.5 mmol) and dried Et2O (2.0 mL) were added to the flask. The product of Example 31 (56.1 mg, 0.4 mmol) in Et2O (2.0 mL) was slowly added to the suspension. The reaction was carried out at room temperature for 4 hours, with excess LiAlH4 decomposed by H2O and H2SO4 (2.0 M, 1.5 mL) slowly added. The product was extracted with Et2O (3 × 4.0 mL), and the combined organic phases were washed with H2O (2 × 1.0 mL), dried, and evaporated. The residue was purified by rapid column chromatography on silica gel to give the product in 87% yield. The enantioselectivity of the product was determined by chiral gas chromatography to be 93% excess (Beta DEX-120, N2 flow rate 1.0 mL / min, 2 min at 70 °C, then 0.1 °C·min). -1 (to 75℃); t r =27.41 and 30.07 min; [α]25 D =12.0 (c 0.20, CHCl3); 1 H NMR(400MHz,Chloroform-d)δ5.41(ddd,J=17.1,10.3,8.5Hz,1H),5.11-5.03(m,1H),4.88(dd,J=10.3,1.6Hz,1H),3.52(dd ,J=14.4,6.8Hz,1H),3.50(dd,J=14.4,7.2Hz,1H),1.39-1.32(m,1H),1.21-1.13(m,1H),0.67(ddd,J=8.1,5.4,2.3Hz,2H); 13 C6H NMR (101 MHz, Chloroform-d) δ 140.6, 112.3, 66.3, 23.0, 20.5, 11.6; HRMS (ESI+) calculated C6H 11 O + ([M+H)) + ):99.0805, Measured value:99.0801.

[0174] Example 33

[0175] Preparation

[0176] The flame-dried Schlenk tube was cooled to room temperature and filled with N2. The product of Example 25 (847.5 mg, 2.3 mmol) and THF (11.5 mL) were added to the flask. The reaction mixture was cooled to -78°C, and freshly prepared LDA (1.0 M in THF, 2.0 equiv) was added dropwise. The reaction mixture was brought to room temperature and stirred until the starting material was completely consumed (detected by TLC). The reaction mixture was cooled to 0°C and treated with a saturated aqueous ammonium chloride solution. The organic phase was separated, and the aqueous phase was extracted three times with Et2O. The combined organic phases were dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give the product in 68% yield. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 96% excess (Chiralcel OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 220 nm); t r = 6.82 and 7.73 min; [α] 25 D =5.9 (c 0.50, CHCl3); 1H NMR(400MHz,Chloroform-d)δ7.93-7.86(m,2H),7.67-7.61(m,1H),7.59-7.53(m,2H),5.39(ddd,J=17.0,10.2,7.8Hz,1H),5.22-5.13(m,1H), 5.07-5.00(m,1H),2.44(ddd,J=8.4,5.4,4.3Hz,1H),2.39(ddd,J=11.9,6.9,3.5Hz,1H),1.69-1.63(m,1H),1.14(ddd,J=8.3,6.4,5.5Hz,1H); 13 C NMR (101MHz, Chloroform-d) δ 140.6, 135.1, 133.4, 129.3, 127.4, 116.7, 40.0, 22.8, 13.0; HRMS (ESI+) calculated C 11 H 13 O2S + ([M+H)) + ):209.0631, Measured value:209.0636.

[0177] Example 34

[0178] Preparation

[0179] At -78°C, n-BuLi (2.5 M in hexane; 1.6 mmol) was added dropwise over 5 minutes to an anhydrous THF (6.0 mL) solution of the product (319.6 mg, 1.54 mmol) from Example 33. The resulting solution was stirred at this temperature for 30 minutes. Me3SiCH2I (3.297 g, 15.4 mmol) was added dropwise over 5 minutes. The reaction mixture was allowed to rise to room temperature over 3 hours. The reaction mixture was stirred at room temperature until the starting material was completely consumed (as detected by TLC). The reaction mixture was cooled to 0°C and treated with a saturated aqueous ammonium chloride solution. The organic phase was separated, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over anhydrous Na2SO4, and the solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give the product in 92% yield, [α]. 25 D = -23.6 (c0.95, CHCl3); 1H NMR(400MHz,Chloroform-d)δ7.91-7.79(m,2H),7.67-7.59(m,1H),7.59-7.48(m,2H),5.45(ddd,J=17.1,10.1,7.6 Hz,1H),5.29-5.12(m,2H),2.62-2.51(m,1H),1.97-1.90(m,1H),0.95-0.88(m,2H),0.82-0.74(m,1H),0.06(s,9H); 13 C NMR (101MHz, Chloroform-d) δ 138.6, 133.5, 133.2, 129.0, 128.7, 119.1, 44.6, 26.8, 18.0, 14.2; HRMS (ESI+) calculated C 15 H 23 O2SSi + ([M+H)) + ):295.1183, Measured value:295.1188.

[0180] Example 35

[0181] Preparation

[0182] At 0°C, a THF solution of BH3 (1.0 M, 0.53 mL, 0.5 equiv) was added to a THF (2.0 mL) solution of the product (312.4 mg, 1.06 mmol) from Example 34. The reaction mixture was stirred at room temperature for 3 hours. After cooling the reaction to 0°C, water (2.0 mL) was added, followed by NaBO3 (1.59 mmol, 1.5 equiv). The reaction was then brought to room temperature and reacted for 1 hour. The solution was diluted with ethyl acetate, and the organic phase was separated. The organic phase was washed with brine, dried over MgSO4, and concentrated. The residue was purified by rapid chromatography to give the product in 79% yield. The enantioselectivity of the product was determined by chiral high-performance liquid chromatography to be 95% excess (Chiralpak OD-H, i-propanol / hexane = 20 / 80, flow rate 1.0 mL / min, λ = 220 nm). r =8.97 and 10.36 min; [α] 25 D = -5.4 (c 0.60, CHCl3); 1H NMR(400MHz,Chloroform-d)δ7.90-7.81(m,2H),7.67-7.60(m,1H),7.58-7.52(m,2H),3.57(t,J=6.5Hz,2H),1.9 0-1.78(m,2H),1.57-1.50(m,2H),1.07(d,J=16.3Hz,1H),0.70(d,J=16.3Hz,1H),0.65-0.59(m,1H),0.05(s,9H); 13 C NMR (101MHz, Chloroform-d) δ 138.6, 133.3, 129.0, 128.8, 62.0, 42.8, 31.0, 20.4, 17.5, 13.3, 0.1; HRMS (ESI+) calculated C 15 H 25 O3SSi + ([M+H)) + ):313.1289, Measured value:313.1290.

[0183] Finally, it should be noted that the terms “comprising,” “including,” or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such process, method, article, or apparatus.

[0184] Although preferred embodiments of the invention have been described, those skilled in the art, upon learning the basic inventive concept, can make other changes and modifications to these embodiments. Therefore, the appended claims are intended to be interpreted as including both the preferred embodiments and all changes and modifications falling within the scope of the invention.

[0185] Obviously, those skilled in the art can make various modifications and variations to this invention without departing from its spirit and scope. Therefore, if these modifications and variations fall within the scope of the claims of this invention and their equivalents, this invention also intends to include these modifications and variations.

Claims

1. A chiral γ-carbonyl phosphate derivative, characterized in that, The general structural formula of the chiral γ-carbonyl phosphate derivative is shown in Formula I: ， in, R 1 It is an alkyl group, and the number of carbon atoms in the alkyl group ranges from 1 to 20; R 2 It is one of sulfonyl or ester groups; Indicates the position of the chiral carbon atom.

2. A method for preparing the chiral γ-carbonyl phosphate derivative according to claim 1, characterized in that, The method includes: Under inert gas protection, substrate 1 and substrate 2 are reacted in an organic solvent and a base at -20 to 110 °C for 0.1 to 96 hours in the presence of an iridium catalyst or an iridium complex to obtain a chiral γ-carbonyl phosphate derivative, as shown in the following reaction formula: ； The preparation method of the iridium catalyst includes: dissolving a metallic iridium salt and a chiral ligand L in a mixed solvent of deoxygenated tetrahydrofuran and deoxygenated n-propylamine, reacting at 50±5 °C for 0.5~1 hours, and then evaporating the solvent under reduced pressure to obtain the iridium catalyst; The method for preparing the iridium complex includes: dissolving a metallic iridium salt and a chiral ligand L in tetrahydrofuran at 20±5 °C, reacting for 0.5 to 1 hour, then adding silver perchlorate and 4-vinyl-1,3-dioxolane-2-one, and reacting at 20±5 °C for 10 to 30 hours to obtain the product, and separating the product by column chromatography to obtain the iridium complex; The structural formula of the chiral ligand L is selected from any of the following: 、 、 、 、 、 。 3. The method according to claim 2, characterized in that, The base is selected from one of the following: alkali metal salts of alcohols, alkali metal salts of amines, alkali metal carbonates, alkali metal hydroxides, or organic bases.

4. The method according to claim 2, characterized in that, The organic solvent is selected from at least one of methanol, ethanol, isopropanol, tert-butanol, sec-butanol, ethyl acetate, isobutyl acetate, isopropyl acetate, n-hexane, cyclohexane, n-heptane, acetone, butanone, diethyl ether, methyl tert-butyl ether, methyl cyclopentyl ether, methyl tetrahydrofuran, tetrahydrofuran, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, toluene, and dioxane.

5. The method according to claim 2, characterized in that, In the reaction system, the concentration of substrate 1 is 0.001~3.0 M, the molar ratio of substrate 1 to substrate 2 is 1:2~10; the amount of iridium catalyst or iridium complex is 0.0001~10 mol% of substrate 1; and the amount of base is 10~1000 mol% of substrate 1.

6. The use of the chiral γ-carbonyl phosphate derivative of claim 1 in the preparation of Hormosirene and (-)-dictyopterene A synthetic precursors, characterized in that the Hormosirene and (-)-dictyopterene A synthetic precursors are selected from... or .

7. The application of the chiral γ-carbonyl phosphate derivative of claim 1 in the preparation of the (R)-MCPA-CoA synthetic precursor, characterized in that the (R)-MCPA-CoA synthetic precursor is... 。

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