236 results about "Enantio selectivity" patented technology

The invention relates to the technical field of biochemical engineering, in particular to a method for preparing chiral alpha-trifluoromethyl alcohol by using imine reductase AtRedAm, trifluoromethyl ketone is reduced into corresponding chiral trifluoromethyl alcohol at an excellent conversion rate by using the imine reductase AtRedAm, and enantioselectivity is high. The reaction depends on an NADPH (Nicotinamide Adenine Dinucleotide Phosphate) coenzyme circulation system, 10% dimethyl sulfoxide is used as a reaction cosolvent, the reaction is carried out in a 100mM (pH = 7.5) phosphate buffer solution for 16 hours, the highest molar conversion rate reaches 99%, and the highest optical purity reaches 95%.

The invention relates to a method for preparing a nerofloxacin chiral piperidylamine intermediate, which comprises the following steps of: carrying out condensation reaction on 5-hydroxy nicotinic acid which is simple and easy to obtain and is used as a raw material and different alcohols, screening through a series of asymmetric catalytic hydrogenation conditions to obtain optimal reaction conditions, and under the conditions, carrying out reaction on various 3, 3 '-dihydroxy nicotinic acid and 3, 3'-dihydroxy nicotinic acid to obtain the nerofloxacin chiral piperidylamine intermediate. The 2, 5-disubstituted pyridine quaternary ammonium salt is reduced into a tetrahydropyridine product, and the C5 site enantioselectivity of the product is excellent. The preparation method comprises the following steps: selecting methyl (R)-1-benzyl-5-hydroxy-1, 4, 5, 6-tetrahydropyridine-3-carboxylic acid methyl ester as a substrate, completely hydrogenating by using platinum dioxide hydrogen, and then carrying out methyl ester reduction, dehydroxylation, Mitsunobu reaction and protecting group removal to obtain a key chiral intermediate for industrial synthesis of a quinolone antibacterial drug nemonofloxacin with high enantioselectivity and high yield.

The present application belongs to the technical field of the synthesis of chiral boron compounds, and in particular relates to an MOF-Cu(II) / CMC composite material, and a preparation method therefor and the use thereof. The preparation method for an MOF-Cu(II) / CMC composite material of the present application comprises: dropwise adding an aqueous solution of sodium carboxymethyl cellulose to an aqueous solution of a bivalent copper salt, performing solid-liquid separation, mixing obtained composite microspheres with an organic solution of trimesic acid, heating the resulting mixture, and subjecting same to solid-liquid separation, so as to obtain an MOF-Cu(II) / CMC composite material. The MOF-Cu(II) / CMC composite material is used in an asymmetric chiral boron addition reaction. The reaction is performed at room temperature, involves mild conditions, is applicable to a wide range of substrates and has a high yield and enantioselectivity. Moreover, the method can achieve the synthesis of a chiral organic boride in a solvent having simple components, providing an efficient new method for the preparation of drug molecules and active intermediates, and also broadening the range of substrates used for the preparation of chiral organic borides.

The invention discloses a chiral alpha-amino acid with a C3 symmetric structure and a preparation method and application thereof, the chiral alpha-amino acid with the C3 symmetric structure provided by the invention is used as an ion pair catalyst, and the structure of the chiral alpha-amino acid with the C3 symmetric structure is more stable than that of other ion pair catalysts due to the C3 symmetric structure; and meanwhile, the chiral phosphamide compound is successfully constructed with relatively high yield (70-80%) and enantioselectivity (80-95%), so that the chiral phosphamide compound has excellent catalytic performance, and the problem that the chiral phosphamide compound is difficult to construct by a traditional ion pair catalyst is solved.

The application belongs to the field of organic synthesis and particularly relates to a synthesis method of polysubstituted indole propionate derivatives. Aryl acetate compounds and sulfonyl indole compounds are used as raw materials, and the reaction is carried out through an isothiourea organic small molecule catalyst. The reaction raw materials are simple and easy to obtain, the reaction conditions are mild, the operation is simple, the reaction time is short, the reaction has good diastereoselectivity and high yield, the synthesis method of the polysubstituted indole propionate derivatives overcomes the defects and deficiencies of the existing synthesis method, and has the characteristics of high efficiency, simplicity and wide universality.

The present application relates to a kind of catalyst composition and its application in catalytic preparation optically active secondary alcohol, the catalyst composition includes chiral ionic bridged aryloxyalkane rare earth complex and additive, the additive is selected from one or more of pyrimidine, N,N-dicyclohexylmethylamine, 4,4'-dipyridyl.The above-mentioned catalyst composition can be used for synergistically catalyzing asymmetric borohydration of chalcone and its derivatives with pinacol borane, and show high catalytic activity and high enantioselectivity, product yield is as high as 99%, ee value can reach 84%, provide a reliable new way for the efficient, high selective synthesis of optically active secondary alcohol.

The application belongs to the field of organic synthesis, and discloses a method for preparing chiral 2-(1,3-diarylallyl)malonate by using a Pd / phosphine oxygen bidentate phosphine phenol ligand catalysis, which comprises the following steps: under a protective atmosphere, mixing P, O-bidentate phosphine phenol ligand, a palladium catalyst, N, O-bis(trimethylsilyl)acetamide, a malonate nucleophilic reagent and an allyl acetate electrophilic reagent in dichloromethane, and reacting to obtain chiral 2-(1,3-diarylallyl)malonate product. The system has the advantages of high enantioselectivity, high catalytic efficiency, wide substrate application range and mild conditions.

The invention discloses a flaky supramolecular chiral copper catalyst based on molecular self-assembly and application thereof, and belongs to the technical field of asymmetric catalysis, the flaky supramolecular chiral copper catalyst is prepared by the following preparation method: dissolving L-ThrC10-20 in a solvent, and stirring to obtain a methanol solution of the L-ThrC10-20; adding ultrapure water into the system, and stirring to obtain a sheet-shaped supramolecular assembly body L-ThrC10-20-NS; and adding Cu < 2 + >, and stirring to obtain the flaky supramolecular chiral copper catalyst L-ThrC16-NS-Cu (II). According to the invention, the flaky supramolecular chiral copper catalyst L-ThrC10-20-NS-Cu (II) assembled on the basis of L-ThrC10-20 and Cu < 2 + > is successfully constructed for the first time, and the catalyst shows obvious enantioselectivity in a Diels-Alder reaction and can be used for efficiently catalyzing to generate an S-endo configuration product.

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 invention discloses a method for olefin enantioselective carbon oxidation through photoelectric synergistic vanadium catalysis, and belongs to the technical field of photoelectric asymmetric catalysis. A bulk chemical organic solvent, an olefin substrate and an N-hydroxyimide substrate are used as raw materials, a vanadium catalyst, an electrolyte and a cathode hydrogen evolution reagent are added, and the enantiomerically enriched olefin carbon oxidation chiral product is prepared under the conditions of electrification and irradiation of an ultraviolet lamp. The method has the characteristics of simple and easily available raw materials, mild reaction conditions, simple and efficient reaction operation, simple and convenient reaction post-treatment, good functional group compatibility, large-scale preparation potential and the like.

The invention discloses a benzoxphosphine ligand and a complex and application thereof. The structure of the benzoxphosphine ligand is shown as a formula (I), in the formula (I), R1 is alkyl or aryl substituted oxazolidinyl or imidazoline, R2 is alkyl and / or aryl, and R3 is at least one of fluorine, carbazolyl and 2, 6-dimethoxyphenyl. According to the benzoxphosphine ligand disclosed by the invention, the metal iridium complex can be used as a catalyst to be applied to an asymmetric hydrogenation reaction of alpha-phenyl vinyl diethyl phosphate, and has excellent activity and relatively high enantioselectivity; moreover, the benzoxphosphine ligand disclosed by the invention can be directly synthesized from simple and easily available chiral aldehyde, and the preparation method is simple and easy to operate.

The invention discloses a biological catalytic synthesis method of chiral 2-amino-1-methylenepropanamide and an enzyme catalyst of the chiral 2-amino-1-methylenepropanamide. According to the present invention, one or more key amino acids in the amide hydrolase derived from Rhodococcus erythropolis AJ270 are subjected to mutation to obtain the mutant, the mutant has characteristics of high or reverse enantioselectivity when the hydrolysis reaction of the racemization 2-substituted-2-amino-1-methylene propanamide substrate is catalyzed, and the chiral compound is obtained with the high ee value; and an enantiomer of a wild type amide hydrolase catalytic product can be obtained. A method for preparing chiral 2-substituted-2-amino-1-methylene propanamide by using the mutant through biological catalysis has the characteristics of simplicity and convenience in operation, high reaction efficiency, mild reaction conditions, high enantioselectivity, easiness in product separation and high product purity, and has a very good application prospect.

This invention belongs to the field of organic synthesis technology and relates to a precursor of an obisec key intermediate and a method for preparing the key intermediate. The method involves a [4+2] cycloaddition reaction of 4-trifluoromethylaniline, propionaldehyde, and N-vinylformamide under the catalysis of chiral phosphoric acid, yielding the obisec key intermediate precursor with high enantioselectivity. N -((2) R 4 S )-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinoline-4-yl)formamide; subsequently, the key intermediate of obisetri can be obtained through a deprotection reaction under acidic conditions. The method provided by this invention uses a small amount of chiral catalyst and commercially available reagents to efficiently obtain the key intermediate of obisetri in just two steps. R 4 S )-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinoline-4-amine; under mild conditions without the need for chiral resolution, the utilization of starting materials is greatly improved, thereby significantly increasing the yield of the target product and the economic efficiency of the process.

The application belongs to the technical field of organic chemical synthesis, and particularly relates to a nitrogen center chiral base derivative, a preparation method and application thereof. The preparation method of the nitrogen center chiral base derivative provided by the application can effectively synthesize a base with only a nitrogen chiral center by using a tetrahydrodibenzo-diazocine compound as a raw material and through chiral phosphoric acid catalyzed amination reaction. Moreover, the synthesis method provided by the application has the advantages of high efficiency, simple steps and strong enantioselectivity, is suitable for industrialized production of chiral bases and derivatives thereof, and provides a new approach for research and application of chiral compounds. Meanwhile, the base derivative prepared by the application is a base molecule with a nitrogen center chirality, and has wide application prospects in the fields of molecular recognition, DNA binding, supramolecular chemistry, material science, asymmetric catalysis and drug development.

The invention relates to the technical field of catalysts, in particular to a chiral diphosphine ligand modification-based ruthenium-carbon hydrogenation catalyst as well as a preparation method and application thereof. The method comprises the following steps: preparing a nitrogen-containing defect carbon carrier; loading ruthenium and reducing; pre-coating the confinement by using an ionic liquid A; introducing a chloride ion template microenvironment; carrying out coordination with a chiral diphosphine ligand; weak coordination anion sizing is realized through the treatment of bis (trifluoromethanesulfonyl) imide silver; and finally introducing chiral ionic liquid B to construct an outer network. The catalyst realizes high enantioselective conversion of a prochiral substrate while maintaining high hydrogenation activity through a multi-layer chiral microenvironment synergistic effect, is excellent in cycling stability, and solves the technical problem that the activity and selectivity of a heterogeneous chiral catalyst are difficult to consider at the same time.

This invention discloses an axially chiral 1,4'-biquinolinone and its derivatives, and a synthetic method thereof. The method uses MBH carbonate and quinoline-2(1 H Using β-ketones as raw materials, (DHQD)₂PYR as catalyst, and DME as solvent, a centrally chiral β-substituted allyl intermediate was synthesized; then, using iron powder as a reducing agent and acetic acid as solvent, enantiomeric enriched centrally chiral γ-lactam compounds were obtained; finally, using DBN as a base and DME as solvent, enantiomeric enriched compounds were obtained. (S) -Axial chiral 1,4'-biquinolinone or its derivatives. The method of this invention has mild reaction conditions, readily available raw materials, high enantioselectivity of the product, and excellent yield. The synthesized 1,4'-biquinolinone or its derivatives can be further used to synthesize novel substituted quinolinone phosphonate compounds, and to synthesize drugs with antibacterial, antimalarial, anticancer, antitumor, or herbicidal activities, showing broad application prospects.

The present invention relates to a process for the enantioselective preparation of chiral 4-substituted 2-oxazolidinones of formula (la) or (lb) via asymmetric hydrogenation of the corresponding 4-substitued 2-oxazolones of formula (II) using a combination of palladium or nickel and a chiral bidentate P-ligand as catalyst. The oxazolidinones can then be converted to important chiral building blocks such as enantiopure chiral aminoalcohols and haloamines via decarboxylative ring opening reaction.

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 application discloses a preparation method of 3,4-dihydropyran derivatives, and a reaction formula is as follows: the unactivated propenal and the weak polar olefin which are simple in structure and low in material cost are used as starting materials, the unactivated propenal and the weak polar olefin which are weak in reactivity can participate in [4+2] cycloaddition, and the 3,4-dihydropyran derivatives with high purity can be prepared; the preparation process is simple in operation, high in yield and excellent in diastereoselectivity, can effectively convert low-cost raw materials into high-value-added compounds, and provides an economic and efficient synthesis strategy for related industries.

The application discloses a kind of plane chiral [2.2] paracyclophanane monophosphine ligand pEPCP and preparation method and application thereof, it is related to chemical catalysis technical field, and its technical scheme main points are as follows: including racemate or enantiomer, the structural formula-I of the monophosphine ligand pEPCP of the application is as follows: [2.2] paracyclophanane skeleton containing monophosphine ligand pEPCP of the application, with two benzene rings in para position by two ethylene connection unique big steric hindrance, electron-rich rigid skeleton, different types ether substituent group is introduced in structure, change the electron cloud density and steric hindrance of aromatic ring directly connected by phosphine ligand.In addition, ether substituent group can also be used as weak coordination group, participate in adjusting ligand chelate dihedral angle.This makes metal, ligand and substrate form the most suitable coordination environment in catalytic process, so that corresponding catalytic reaction has the advantages such as high reactivity, good enantioselectivity, substrate universal range is wide, especially suitable for transition metal catalyzed asymmetric coupling reaction, with economic practicability and industrial application prospect.

The application discloses an allyl compound containing chiral monofluoromalonate diester and an asymmetric catalytic synthesis method and application thereof, the compound has the structure shown in the following formula, has potential biological activity and pharmacodynamic activity, provides strong technical support for development of new drugs, and has high practical value; the synthesis method is started from 1,3-diene and a nucleophilic reagent fluoromalonate diester as raw materials, and the chiral monofluoromalonate diester substituted allyl compound is efficiently synthesized through a chiral metal catalyst. The method has the following characteristics: the raw material is cheap and easy to obtain; no base needs to be added, the reaction condition is mild, and the operation is simple; the substrate has a wide application range, excellent enantioselectivity can be obtained, and good to excellent yield is achieved. The product prepared by the application is a useful fluorine-containing building block, and a variety of fluorine-containing compounds can be synthesized through simple chemical conversion.

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.

The application discloses a method for synthesizing a chiral secondary phosphine oxide with a conjugated dienyl phosphorus center through desymmetrization. The method is that a primary phosphine oxide reacts with an alkyne to obtain the chiral secondary phosphine oxide with the conjugated dienyl phosphorus center under the joint catalysis of zero-valent nickel and a ligand and the action of an additive. The method realizes the preparation of the chiral secondary phosphine oxide with the conjugated dienyl phosphorus center with high enantioselectivity and specific chemical selectivity through the joint catalysis of the zero-valent nickel and the ligand.

The application discloses a kind of chiral PEG-Ag6D / LSP6 cluster-based nanoparticles, method and application, method includes: S1, the preparation of chiral nanocluster, in mixed solvent silver salt and thiazolidine thione ligand is added, and the crystal of chiral silver nanocluster is obtained by volatilization;S2, a certain amount of amphiphilic polymer DSPE-PEG2000 and chiral silver nanocluster are dissolved in organic solvent, then added to a certain volume of aqueous solution;S3, under the condition of violent stirring, reaction is carried out until organic solvent is completely removed, filtration is carried out, and the product is obtained;The chiral PEG-Ag6D / LSP6 cluster-based nanoparticles prepared in the application has good biocompatibility, rapid response to biological thiol, strong anti-interference ability and low detection limit, and is suitable for high-throughput equipment, can be used for biological thiol distinction, enantioselective chiral recognition and biological thiol quantitative detection in plasma, and as potential nanomedicine and exhibit chiral-dependent anti-tumor effect.

The invention belongs to the technical field of biochemistry, and particularly relates to a method for catalytically synthesizing a chiral nitrogen heterocyclic compound by a biological enzyme. The invention develops a method for obtaining a chiral nitrogen heterocyclic compound with high enantioselectivity by catalyzing an easily-obtained N-acyloxy amine compound as a nazein precursor to carry out C (sp3)-H amination cyclization reaction by taking an enzyme containing heme as a catalyst. The enzyme catalysis method is mild in reaction condition, simple in technical requirement, wide in substrate universality, high in product enantioselectivity and green, efficient and economical in synthesis process. The nitrogen-containing heterocyclic compound prepared by the method disclosed by the invention has the advantages of better reaction yield, excellent regioselectivity, wide substrate range and good functional group compatibility, and can be applied to synthesis and modification of some drug intermediates.

The invention relates to a synthesis method of a chiral trifluoromethyl allyl tertiary alcohol compound, which comprises the following steps: under the protection of nitrogen, taking alkyne and trifluoromethyl ketone as raw materials, taking metal cobalt salt and an organic ligand as catalysts, taking Hanus ester as a reducing agent, and reacting in the presence of excessive organic solvent, photosensitizer and organic alkali to obtain the chiral trifluoromethyl allyl tertiary alcohol compound. And carrying out illumination reaction to obtain the chiral trifluoromethyl allyl tertiary alcohol compound. The method has the advantages of simple and easily available reaction raw materials and reagents, mild and easily controlled conditions, high atom economy, no need of noble metal catalysis, wide substrate application range, high regioselectivity, stereoselectivity and enantioselectivity, and wide application prospect.

The invention discloses a chiral P, N, N-tridentate ligand based on a ferrocene skeleton as shown in a formula I, a preparation method of an iridium catalyst containing the ligand and application of the ligand in preparation of a carbon-nitrogen axial chiral compound and a diltiazem intermediate. According to the present invention, the chiral P, N, N-tridentate ligand based on the ferrocene skeleton and the metal iridium precursor [Ir (COD) Cl] 2 are subjected to complexation to obtain the complex as the iridium catalyst, and the catalyst can be used as the iridium catalyst with characteristics of high yield (up to 99%), high enantioselectivity (up to gt; 99% ee) and high diastereoselectivity (up to gt; according to the method, N-aryl indolal or N-aryl indolone is subjected to asymmetric hydrogenation by using N-aryl indolal or N-aryl indolone (R1, R2, R3, R4, R5, R6, R7, R7, R8, R9, R9, R9, the catalyst can also be applied to asymmetric synthesis of diltiazem intermediate (2R, 3S)-3-(4-methoxyphenyl)-2, 3-epoxidized propionate, has the advantages of short synthesis route, high yield, good stereoselectivity (as high as 99% ee, 97 / 3dr) and the like, and has better economic and social benefits.

The application discloses a method for synthesizing an alpha-position chiral nitrogen heteroaromatic ring under the synergistic catalysis of a chiral phosphoric acid and a Lewis acid, and the method comprises the following steps: taking a nitrogen heteroaromatic ring olefin I as an electrophilic reagent, taking an aryl alkyl boronic acid II as a carbon nucleophile, and under the synergistic catalysis of a Lewis acid catalyst and a chiral phosphoric acid catalyst, in the presence of an organic solvent, an additive and a proton source, performing a conjugate addition-asymmetric protonation reaction to generate an alpha-position chiral nitrogen heteroaromatic compound shown in formula V, and the reaction is shown as follows: The application provides a conjugate addition-asymmetric protonation strategy for a nitrogen heteroaromatic ring olefin, which is synergistically catalyzed by a chiral phosphoric acid and a Lewis acid (Fe(OTs)3) and involves an organic boron reagent, a series of alpha-position chiral nitrogen heteroaromatic compounds are successfully synthesized by using the catalytic system, the highest enantioselectivity reaches 98% ee, and good universality is shown for aryl, heterocyclic and polysubstituted substrates, and the bottleneck problem of low reactivity of 1,1-disubstituted substrates in a traditional method is effectively overcome.

The present invention relates to a process for the preparation of optically active 4-substituted 1, 2, 3, 4-tetrahydroquinoline, said process comprising the enantioselective hydrogenation of the corresponding 4-substituted 1, 2-dihydroquinoline in the presence of a chiral iridium (P, S)-ligand catalyst.

The application provides a chiral 2-position disubstituted indoline compound and a synthesis method and application thereof. The application uses a simple structure palladium catalyst and a chiral ligand as a catalyst system, and uses a newly designed allyl benzoxazinone as a raw material to perform a palladium catalyzed intramolecular asymmetric cyclization reaction, so that efficient asymmetric synthesis of the chiral 2-position disubstituted indoline compound is realized. The synthesis method is simple, the reaction condition is mild, the cost is low, and the efficiency is high; the raw material is cheap and easy to obtain, atom economy is good, and the substrate is widely applicable; the target product has high yield and high enantioselectivity; the chiral 2-position disubstituted indoline compound obtained by the application has excellent inhibition effect on bladder cancer cells, provides a scientific basis for developing a new candidate drug for treating bladder cancer, and has important significance for the treatment of bladder cancer.