303 results about "Chiral ligand" patented technology

The invention discloses a method for respectively realizing asymmetric hydroamination and migration hydroamination of olefin by using nickel and ligand combined catalysis, and belongs to the field of organic chemistry and medicinal chemistry. Under the action of a metal nickel source, a chiral ligand, a hydrogen source, an additive and the like, olefin and azide amination reagents protected by different carbonates are used as amine sources to react in an organic solvent, and a series of chiral amine and alkylamine compounds are obtained with excellent enantioselectivity and good yield. Cheap transition metal nickel is used as a catalyst, simple and easily available alkene and carbonic ester protected azide amination reagents are used as raw materials, conditions are mild and simple, functional group compatibility is good, and operation is easy and convenient.

The invention discloses a method for preparing a chiral furanone ester derivative, which comprises the following steps: adding a metal catalyst into a solvent, sequentially adding a carboxylic acid compound I or a carboxylic acid compound II and a butene lactone compound III, introducing inert gas, stirring, post-treating and purifying to obtain a chiral furanone ester compound IV; the palladium catalysis system is composed of palladium salt and a chiral ligand V, and the chiral ligand has a structure shown in a formula V.

The invention provides a method for constructing planar chiral [2, 2] paracyclophane by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution, which comprises the following steps: by using a cobalt catalyst, a chiral ligand and an additive, taking a graphite felt electrode as an anode and taking a platinum sheet electrode as a cathode, carrying out racemization on [2, 2] paracyclophane under the condition of direct-current electrolysis, so as to obtain the planar chiral paracyclophane. The preparation method comprises the following steps: carrying out asymmetric carbon-hydrogen bond dehydrogenation coupling / kinetic resolution on 2, 2] paracyclophane formamide and aryl acid, and after the reaction is finished, carrying out corresponding post-treatment to obtain planar chiral [2, 2] paracyclophane formamide and planar chiral oxopara-[2, 2] paracyclophane; according to the method, electrochemical synthesis of planar chiral oxara-[2, 2] paracyclophane is realized through a method for catalyzing asymmetric carbon-hydrogen bond activation by virtue of a crustal high-yield transition metal, a reaction substrate is wide in universality and excellent in stereoselectivity, and a product and a split and recycled raw material can have an excellent ee value (up to gt; 99% ee) and a splitting factor (up to 1057).

The invention belongs to the technical field of asymmetric catalysis, and discloses a chiral phosphine nitrogen-nitrogen tridentate ligand based on a ferrocene skeleton as well as a preparation method and application of the chiral phosphine nitrogen-nitrogen tridentate ligand. The structural formula of the ligand is shown as (I) or an enantiomer (II) of the ligand. The preparation method comprises the steps of acylation reaction, oxazoline ring construction, aldehyde group introduction, reductive amination and the like, and application in asymmetric hydrogenation reaction, such as asymmetric hydrogenation of aryl ketone. The ligand has a plurality of chiral factors, simultaneously has a potential hydrogen bond donor, forms secondary interaction with a substrate in an asymmetric catalytic reaction, can further stabilize a reaction transition state, is an efficient novel chiral P, N, N-ligand, has the advantages of high reaction activity, good stereoselectivity, wide substrate range and the like, and has a wide application prospect. # imgabs0 #

The invention discloses a chiral circularly polarized crystalline luminescent material and a synthesis method and application thereof, and belongs to the technical field of new materials. The chemical formula of the chiral circularly polarized crystalline luminescent material is (R-BINAP) 2M < 2 > X < 2 > or (S-BINAP) 2M < 2 > X < 2 > as shown in a formula II, wherein BINAP is 1, 1 '-binaphthyl-2, 2'-bisdiphenylphosphine, M < + > represents at least one heavy metal ion of Cu < + > and Ag < + >, and X <-> represents at least one surface halide ion of Cl <->, Br <-> and I <->. Due to the diphosphine chelating coordination effect of the chiral ligand, the chiral circularly polarized crystalline light-emitting material has relatively high asymmetric light-emitting factors, thermal stability and machinability. The problem that large brightness loss is usually accompanied by a traditional physical method from a non-polarized light source to a polarized light source is solved, and the method shows important application prospects in the fields of 3D display, optical storage, optical anti-counterfeiting, asymmetric synthesis and the like.

The invention discloses a copper oxide / cuprous oxide heterogeneous nano-material with chiral morphology and a preparation method thereof, and the method comprises the following steps: 1, mixing a copper salt aqueous solution and a surfactant aqueous solution to obtain a mixed solution A, taking a chiral ligand aqueous solution to add into the mixed solution A under a stirring state, and stirring at room temperature to obtain a copper oxide / cuprous oxide heterogeneous nano-material; a copper ion reaction precursor solution is obtained; and 2, adding a sodium hydroxide aqueous solution into the copper ion reaction precursor solution, stirring at room temperature to obtain a mixed solution B, transferring the mixed solution B into a hydrothermal reaction kettle, putting the hydrothermal reaction kettle into a drying oven, reacting at 120-160 DEG C for 2-6 hours, after the reaction is finished, centrifugally separating out a precipitate, and sequentially washing and drying in vacuum to obtain the copper ion catalyst. The copper oxide / cuprous oxide heterogeneous nano material with chiral morphology is obtained. The preparation method is simple, low in cost and easy to implement, and the obtained chiral copper oxide / cuprous oxide heterogeneous nano material has good structural stability and crystallinity.

The present invention relates to the technical field of nanomaterials, and provides a CdSe@ZnS quantum dot and a preparation method thereof. The method comprises: dissolving oil-soluble CdSe quantum dots in a non-polar organic solvent to obtain a seed solution; adding a zinc ion aqueous solution to a chiral ligand molecule aqueous solution for mixing, using sodium hydroxide to adjust the pH of the mixed aqueous solution until the white flocs disappear, and then adding a sulfur ion aqueous solution in an equal molar ratio to the zinc ion aqueous solution, mixing evenly, and obtaining a shell growth aqueous solution; then, adding the shell growth aqueous solution to the seed solution to form a two-phase interface, stirring for 6 to 24 hours at a temperature of 25°C to 45°C to form CdSe@ZnS quantum dots. The CdSe@ZnS quantum dots prepared by the present invention not only have excellent chirality and fluorescence properties, the fluorescence quantum yield can reach 67.2%, the chiral asymmetry factor can reach 0.01, but also have good water solubility and biocompatibility.

The invention discloses a selective asymmetric hydrogenation method of 4-substituted-1, 2-dihydroquinoline and application of the selective asymmetric hydrogenation method, and relates to the technical field of pesticide chemistry. According to the present invention, in the presence of the chiral ligand and the rhodium catalyst, the 4-substituted-1, 2-dihydroquinoline is subjected to the selective asymmetric hydrogenation reaction, and the selective asymmetric hydrogenation method has advantages of simple steps, high conversion rate and high enantioselectivity.

The invention discloses a zinc sulfide nano material with chiral morphology and a preparation method thereof, and the method comprises the following steps: 1, adding an alkali source solution into a chiral ligand aqueous solution, and carrying out ultrasonic treatment at 30 DEG C to obtain a chiral ligand reaction precursor solution; 2, adding a zinc salt solution into the chiral ligand reaction precursor solution, and stirring to obtain a mixed turbid solution; 3, placing the mixed turbid liquid in a water bath kettle at the temperature of 15-50 DEG C, keeping the temperature for 3-30 minutes, separating out precipitates, washing and freeze-drying to obtain a zinc-chiral ligand complex nano material; and 4, transferring the zinc-chiral ligand complex nano-material to a quartz porcelain boat, putting the quartz porcelain boat into a tubular furnace, heating from room temperature to 300-700 DEG C at a heating rate of 1-5 DEG C / min in a protective atmosphere, calcining for 1-12 hours, and cooling to obtain the zinc sulfide nano-material with chiral morphology. The preparation method is simple, easy to control, low in cost and high in universality, and the prepared chiral zinc sulfide nano material has good crystallinity and stability.

The application relates to a chiral NSiN ligand based on a phenyloxazoline skeleton, a preparation method and application thereof, wherein the chiral NSiN ligand is prepared from a chiral phenyloxazoline bromide with R or S configuration through lithiation and silylation. The chiral NSiN ligand can be used in transition metal catalyzed asymmetric synthesis, and is used in catalyzing an allylic sulfonylation reaction with a cobalt catalyst, and shows high reaction activity and high stereoselectivity.

A quinazolinone catalyst with both N-N and C-C axis chirality and its synthesis method and application, its chemical structural formula is shown in Formula 4; Synthesis method: using indole-derived o-aminobenzamide and 1-naphthaldehyde derivative as raw materials, using molecular sieve as dehydrating agent, bromobenzene as reaction solvent, stirring for 4h under the catalysis of chiral phosphoric acid and 10°C, then adding ethyl acetate, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, stirring for 10h under room temperature, TLC tracking reaction to complete formula 3 compound; using formula 3 compound, phenylsilane, trifluoromethanesulfonic acid as raw materials, adding toluene, stirring reaction under 100°C, TLC tracking reaction to end to obtain formula 4 compound. The catalyst prepared by the present invention can be used as a chiral ligand in transition metal-catalyzed asymmetric allylation reaction, with excellent stereoselectivity control effect; the method has mild reaction conditions, low cost and high enantioselectivity.

This invention discloses a novel chiral bipyridine ligand, its synthesis method, and its application. The novel chiral bipyridine ligand is selected from compounds with the following structures: The chiral ligand of this invention has been successfully applied in the copper-catalyzed asymmetric ring-opening / cross-coupling reaction of cyclic diaryl iodine and secondary amine, yielding the product with excellent yield and ee value.

The invention provides a 1-phosphorus-doped norbornene-dimethyl xanthene chiral ligand as well as a synthesis method and application of the 1-phosphorus-doped norbornene-dimethyl xanthene chiral ligand. The structural formula of the chiral ligand is shown as a formula III and a formula III ': # imgabs0 #, a group R is C1-6 alkyl, C1-6 alkoxy, C1-6 alkenyl, phenyl, halogenated phenyl, C1-6 alkyl substituted phenyl or C1-6 alkoxy substituted phenyl, and a group R1 is C1-6 alkyl. The chiral ligand serves as a chiral phosphine ligand with a novel structure, three completely bound P-C bonds are formed through introduction of a rigid framework, the scientific problem that a phosphorus chiral center is easy to racemize is successfully solved, the phosphorus chiral ligand can be widely applied to asymmetric reactions such as asymmetric cyclization catalyzed by metal, and the phosphorus chiral ligand has a wide application prospect. And the method has a wide commercial application prospect. The synthesis method of the chiral ligand comprises the steps that the 9, 9-dimethyl xanthene compound and the 1-phosphorus-doped norbornene amine compound serve as raw materials, the chiral ligand is generated through H [1, 5] migration and phosphorus-doped D-A reaction, and the synthesis method is simple, good in feasibility and high in yield.

This invention discloses a chiral [oxyindole-pyrrolidine-β-lactam] bispirocyclic compound containing trifluoromethyl groups, with the following structural formula: The preparation includes the following steps: 1. Sequentially adding a metal catalyst, a chiral ligand, a base, indigo-derived trifluoromethylimine ylide, and 3-methylene β-lactam, followed by the addition of an organic solvent to obtain a mixture. The mixture is stirred at a reaction temperature of 0℃ to 50℃. 2. After the reaction is complete, the chiral [oxyindole-pyrrolidine-β-lactam] bispirocyclic compound containing trifluoromethyl groups is obtained through post-processing. The chiral [oxyindole-pyrrolidine-β-lactam] bispirocyclic compound containing trifluoromethyl groups prepared in this application lays a material foundation for in-depth drug activity research based on new drug development.

The invention discloses a method for preparing a chiral benzhydrol compound through asymmetric hydrogenation of o-amido benzophenone under catalysis of rhodium. The chiral rhodium catalyst is generated in situ from a metal rhodium salt and a chiral phosphine-phosphoramidite ligand in various solvents. Compared with other methods for synthesizing chiral benzhydrol, the method has the characteristics of cheap catalyst, easiness in preparation of chiral ligand, mild reaction conditions, simplicity and convenience in operation, high yield, high enantioselectivity and the like, and can be applied to large-scale preparation of chiral benzhydrol compounds. The method is also suitable for efficient preparation of the rice plant growth regulation inhibitor (S)-Inabenide, the yield can reach 92%, the enantioselectivity can reach 96%, and the method has good industrial application prospects.

The present invention relates to the technical field of material chemistry, and in particular to a chiral nickel oxide nanoparticle and a preparation method thereof, wherein the preparation method comprises the following steps: S1, preparing a transition metal nickel ion reaction precursor solution and an oxalate ion reaction precursor solution; S2, adding the oxalate ion reaction precursor solution to the transition metal nickel ion reaction precursor solution to obtain a mixed solution; S3, stirring and heat-insulating in a water bath until a mixed turbid liquid is obtained; S4, centrifuging the mixed turbid liquid, and washing the centrifuged precipitate with deionized water and ethanol to obtain a chiral nickel oxalate nanomaterial; and S5, calcining to obtain a chiral nickel oxide nanoparticle. The present invention combines an inorganic compound with a chiral ligand to synthesize a chiral nickel oxalate precursor, and then calcining the chiral nickel oxalate precursor to obtain the chiral nickel oxide nanoparticle; a simple and efficient coprecipitation method and a calcination method are adopted, and the reaction conditions are easy to implement, the process is simple, the cost is low, and the chiral nickel oxide nanoparticle has good universality.

The invention discloses a novel C2 symmetric chiral bisamide ligand and a preparation method and application thereof, the ligand has a structure as shown in # imgabs0 #, Ar is aryl, the relative positions of two sulfur in the general formula are different, * represents a chiral center, R is 4-methylbenzyl, 4-bromobenzyl, 2, 6-dimethylbenzyl, methyl or benzyl, and n represents 1 or 2. Dithiophenol and (2S, 3S)-2, 3-diphenylaziridine react to obtain an intermediate, and the intermediate and nitrogen-substituted chiral cyclic amino acid or 2-diphenylphosphinobenzoic acid are subjected to dehydration condensation to obtain various ligands with novel structures. A catalyst formed by complexing the ligand and an allyl palladium chloride dimer can be used as a chiral ligand for efficiently catalyzing an asymmetric allyl alkylation reaction.

The invention discloses chiral gold nanoparticles for an alkaline electrolysis water oxygen evolution reaction catalyst and a synthesis method and application thereof, L-shaped gold nanoparticle branched particles and D-shaped gold nanoparticle branched particles of chiral multi-branched gold nanoparticles are synthesized, and the chiral multi-branched gold nanoparticles are further used for catalyzing an oxygen evolution reaction. In the synthesis process, the chiral strength of a sample can be regulated and controlled by regulating and controlling the concentration of the chiral ligand, and the chiral strength can be reflected through the signal strength of circular dichroism. Compared with the prior art, the preparation method is simple, the manufacturing cost is low, and the catalytic performance of the oxygen evolution reaction is excellent. The oxygen evolution reaction performance of the L-shaped gold nanoparticle branch type particles in the sample is far superior to that of D-shaped gold nanoparticle branch type particles. Under the current density of 10 milliamperes per square centimeter, the L-shaped gold nanoparticle branch type particles reach 355.1 millivolts and 449.7 millivolts, the Tafel slope reaches 61.72 millivolts per ten degrees, the stability can be kept for 24 hours under the current density of 10 milliamperes per square centimeter, and the stability is good.

The application belongs to the technical field of asymmetric catalytic synthesis, and particularly relates to an alpha-carbon chiral phosphine compound and a preparation method thereof. In a protective gas atmosphere, an asymmetric boron protonation reaction is carried out on a dienyl phosphine oxide compound shown in a structure of formula II, pinacol borate, a copper (I) catalyst, a chiral ligand, an organic alkaline compound and a proton additive in a polar organic solvent to obtain an alpha-carbon chiral phosphine compound shown in a structure of formula I; the chiral ligand is a cyclic phosphine ligand (S, S)-Ph-BPE or a cyclic phosphine ligand (R, R)-Ph-BPE. The preparation method provided by the application can synthesize the alpha-carbon chiral phosphine compound shown in the structure of formula I with high yield and excellent enantioselectivity, the synthesis method is simple and low in cost, and the alpha-carbon chiral phosphine compound can be further converted into a new optically active product.

The invention discloses a chiral indolone spirochroman compound as well as a synthesis method and application thereof, and belongs to the field of organic chemical synthesis and medicines. The structure of the compound is an indolone spirochroman skeleton with a C3-site spiro chiral center, and the synthesis method comprises the following steps: at room temperature, dissolving palladium and a chiral ligand (L) in an organic solvent, stirring, sequentially adding acetenyl cyclic carbonate (I) and a 3-substituted indolone derivative (II), stirring to react, and separating and purifying to obtain the compound. The compound provided by the invention can be efficiently converted into other indolone spirochroman compounds with novel structures through simple reaction, and has good potential application value in the research of antitumor drugs; the synthesis method disclosed by the invention is novel and has the advantages of simplicity in operation, mild reaction conditions, good substrate universality, high yield, high stereoselectivity and the like.

The application discloses a rhodium-catalyzed desymmetrization hydroformylation method for constructing polychiral center carbon ring nucleosides. The method for constructing polychiral center carbon ring nucleosides comprises the following steps: under the condition of an inert atmosphere, an acetylacetone dicarbonyl rhodium metal precursor and a chiral ligand are added into an organic solvent to prepare a catalyst solution, the catalyst solution is mixed with a substrate, and a reaction is carried out under the condition of a hydrogen atmosphere and a carbon monoxide atmosphere; after the reaction is completed, filtration and purification are carried out, and polychiral center cycloalkyl aldehyde is obtained; and the aldehyde group is converted to obtain the polychiral center carbon ring nucleosides. The method for constructing polychiral center carbon ring nucleosides has the advantages of high selectivity, wide substrate compatibility, high reaction efficiency, easy conversion of products, and the like. The whole reaction process can obtain polychiral center cycloalkyl aldehyde in one step with extremely high enantioselectivity and diastereoselectivity, the aldehyde group is converted, polychiral center carbon rings can be obtained with high yield, high dr value and high ee value, and the method is simple and easy to operate.

The invention discloses a preparation method of a cobalt-based chiral enantiomer superparticle and the cobalt-based chiral enantiomer superparticle, and the preparation method comprises the following steps: stirring a mixture containing a cobalt source solution and an amino acid solution for reaction under an alkaline condition to obtain the cobalt-based chiral enantiomer superparticle, amino acid in the amino acid solution is L-cystine and / or D-cystine. The cobalt-based superstructure particles synthesized by the method have good chiral optical activity in a visible light region and a near-infrared light region, and have important guiding significance for preparing chiral enantiomer structure materials and exploring an assembly mechanism generated by a chiral ligand-induced chiral structure.

The invention mainly relates to the technical field of heterocyclic compounds. According to the production process of lobeline hydrochloride, LBL00 and a glutaraldehyde aqueous solution are used as starting materials, LBL00 is hydrolyzed to obtain LBL01, LBL01 and glutaraldehyde react to construct a key intermediate LBL02, LBL02 is reduced to obtain LBL03, the intermediate LBL03 is subjected to catalytic acylation through a chiral ligand to obtain an intermediate LBL04, the intermediate LBL04 is oxidized to obtain an intermediate LBL05, the intermediate LBL05 is hydrolyzed to obtain an intermediate LBL06, and the intermediate LBL06 is subjected to hydrolysis to obtain the lobeline hydrochloride. And decolorizing the intermediate LBL06, recrystallizing, drying and sub-packaging to obtain LBL, namely lobeline hydrochloride. Compared with the prior art, the materials LBL00 and glutaraldehyde are the main chemical structure fragments of LBL, the reaction steps can be reduced by selecting the materials as the starting materials, and the risk of impurity increase in the synthesis process can be avoided.

The application discloses a five-membered ring containing alkynyl or triazole functional group P The chiral phosphine oxide compound is obtained through Domino Heck-Sonogashira cascade reaction by taking a prochiral tertiary phosphine oxide compound containing a double ethylene group and phenylacetylene as raw materials, transition metal palladium catalyst and chiral TADDOL phosphoramidite ligand under the protection of inert gas P The chiral phosphine oxide compound has a product yield of 96% and an enantioselectivity ee value of 99%, and a diastereoselectivity dr value of greater than 20:1. The application adopts an asymmetric desymmetrization strategy, uses a Heck reaction to start and a Sonogashira reaction to end a cascade reaction, simultaneously constructs P The chiral and quaternary carbon chiral center has mild reaction conditions, simple operation and good substrate universality, provides a compound skeleton with diversity, and is successfully applied to a palladium-catalyzed asymmetric allyl substitution reaction as a chiral ligand.

According to the method, an enamine intermediate (2Z)-4-oxo-4-[3-(trifluoromethyl)-5, 6-dihydro-[1, 2, 4] triazolo [4, 3-a] pyrazine-7 (8H)-yl]-1-(2, 4, 5-trifluorophenyl) butyl-2-ene-2-amine is used as an initial raw material, and the Sitagliptin is synthesized through synergistic catalysis asymmetric hydrogenation of a cobalt catalyst and a chiral ligand. The R-configuration sitagliptin is prepared by one step, the reaction yield and stereoselectivity are high, the catalytic reaction effect is good, the cost is low, and the method is suitable for industrial large-scale production.

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing a chiral allene compound from aromatic hydrocarbon and alkyne. A simple aromatic hydrocarbon compound and thianthrene-S-oxide are designed to construct an aryl thianthrene salt in situ under the action of an electrophilic activation reagent, then the aryl thianthrene salt constructed in situ under catalysis of a palladium catalyst and a chiral ligand is subjected to an asymmetric Heck reaction with alkyne, and the tri-substituted chiral allene compound is rapidly and efficiently constructed. The method is mild in condition, wide in substrate range and excellent in enantioselectivity and yield, and meanwhile, chiral allene fragments can be introduced into salicin and indometacin which have anti-inflammatory and analgesic activities.

The invention discloses a chiral oxazoline ligand containing an indole skeleton as well as a synthesis method and application of the chiral oxazoline ligand. The chiral ligand has a structure as shown in a formula 1, and R1 is selected from one of alkyl, substituted alkyl, aryl and substituted aryl. The chiral oxazoline ligand of the indole skeleton can realize high-enantioselectivity Friedel-Crafts reaction of an indole skeleton compound, the reaction is one of important carbon-carbon bond forming methods in organic synthesis, and a chiral indole derivative can be efficiently generated; the chiral indole derivative has important application in synthesis of natural products and bioactive compounds. In addition, raw materials used for preparing the compound are cheap and easy to obtain, the synthesis route is short, the related reaction is a basic organic chemical reaction, the process is simple and convenient, the product is easy to separate and purify, and the method is suitable for large-scale synthesis.

The invention provides a chiral delta-lactam compound as well as a preparation method and application thereof. The preparation method of the chiral delta-lactam compound comprises the following steps: taking a 1, 4, 2-dioxazole-5-ketone derivative and a nucleophilic reagent as raw materials, and reacting under the action of a chiral metal catalyst and an additive to generate the chiral delta-lactam compound. According to the synthesis strategy, under the catalysis of a chiral Ir (III) catalyst, an olefin part in a substrate molecule and electrophilic metal nitrogen are subjected to an electrophilic addition reaction to generate a carbocation intermediate, then 1, 2-negative hydrogen migration is carried out under the promotion of a chiral ligand, more stable aza carbocations are formed, and the chiral Ir (III) compound is synthesized. And a nucleophilic reagent captures the compound to form a delta-lactam compound containing a continuous gamma, delta-chiral center. The method has excellent yield, diastereomer selectivity and enantiomer selectivity, and is compatible with various carbon, nitrogen and oxygen nucleophilic reagents and biological related molecules. The invention provides a brand-new efficient route for synthesis of the chiral delta-lactam compound.

The application discloses chiral bis-thiophene-bis-nitrogen-oxygen ligands BbTh-2NO and BTh-2NO. The ligands comprise bis-thiophene groups and nitrogen-oxygen groups (sulfur atoms of the bis-thiophene and oxygen atoms of the nitrogen-oxygen groups belong to electron-rich coordination sites), can form six-membered ring coordination with Lewis acid soft metal palladium, thereby generating chiral ligand metal palladium complexes, and are applied as chiral ligands in asymmetric catalytic reactions. Therefore, the application has important application value in the field of asymmetric catalytic synthesis, and a synthesis method thereof is very economical and simple. The application also has good air stability, wide applicability and good compatibility for various substituents.

The invention relates to the technical field of asymmetric catalysis, and in particular to a chiral bidentate nitrogen ligand based on a cinchona alkaloid skeleton, a preparation method and an application thereof. The compound is used to catalyze an asymmetric hydrogenation reaction of a heterocyclic aromatic ketone. The metal catalytic reaction product co-modified with the chiral ligand and an achiral phosphine ligand has a high conversion rate, and the enantioselectivity can reach 99.9%. The chiral bidentate nitrogen ligand is prepared by using cinchona alkaloid as a raw material, the raw material is cheap and easy to obtain, the preparation reaction process is simple, and the compound is stable in an air environment, and the compound has a very high application value.