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40 results about "Kinetic resolution" patented technology
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In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials. This enantiomeric excess (ee) of the unreacted starting material continually rises as more product is formed, reaching 100% just before full completion of the reaction. Kinetic resolution relies upon differences in reactivity between enantiomers or enantiomeric complexes. Kinetic resolution is a concept in organic chemistry and can be used for the preparation of chiral molecules in organic synthesis. Kinetic resolution reactions utilizing purely synthetic reagents and catalysts are much less common than the use of enzymatic kinetic resolution in application towards organic synthesis, although a number of useful synthetic techniques have been developed in the past 30 years.
Method for regulating and controlling dynamic kinetic resolution of spiral polycyclic aromatic hydrocarbon based on inorganic chiral surface and application
PendingCN121288352AVacuum evaporation coatingSolid sorbent liquid separationPolycyclic aromatic hydrocarbonKinetic resolution
The invention provides a method for regulating and controlling dynamic kinetic resolution of spiral polycyclic aromatic hydrocarbon based on an inorganic chiral surface and application, and the method comprises the following steps: S1, rotating a substrate clockwise or anticlockwise, and depositing an inorganic material on the substrate by adopting a physical vapor deposition method to obtain an inorganic chiral nano material layer; wherein the contact angle between the inorganic material and N, N-dimethylformamide is less than 22 degrees, and the deposition angle and the normal direction of the substrate form an angle of 86 degrees or 0 degree; s2, dissolving spiral polycyclic aromatic hydrocarbon molecules needing to be split into N, N-dimethylformamide to obtain a solution; then dropwise adding to the surface of the inorganic chiral nano material layer to obtain a sample; and S3, annealing the sample at 40-50 DEG C, and obtaining the homochiral aggregate after the solvent is completely evaporated. The technical scheme provided by the invention is high in controllability, strong in universality and good in stability, and can be used for efficiently preparing chiral compounds with specific configurations.
Owner:SHENZHEN POLYTECHNIC
A one-pot method for the chemical / enzymatic cascade preparation of s-delta-substituted caprolactams
The application discloses a kind of S-delta-substituted caprolactam chemical / enzyme series preparation method, and the specific preparation method is: 1-substituted high allyl amine occurs dynamic kinetic resolution reaction with acrylic ester compound under the catalysis of alkaline protease (special treatment) and generates S-acryl (1-substituted high allyl) amine, then the product occurs intramolecular olefin metathesis under the catalysis of Grubbs reagent and finally generates S-delta-substituted caprolactam shown in formula (1), wherein, substituent R is phenyl, halogenated phenyl or C2-C12 alkyl.The application has mild reaction condition, is conducive to reducing the equipment requirement of preparation process, improves synthesis safety and economy;Secondly, the reaction course of the method is simple, and single configuration S-delta-substituted caprolactam can be obtained by one-pot reaction, with very high atom economy.
Owner:ZHEJIANG UNIV OF TECH +1
A method for asymmetric synthesis of ortho-halogenated alcohol compounds
ActiveCN117126126BOrganic compound preparationHydroxy group formation/introductionChemical synthesisAlcohol
The application belongs to the technical field of chemical synthesis, and particularly relates to a method for asymmetrically synthesizing adjacent halogenated alcohol compounds. The cis adjacent halogenated alcohol compound is prepared through catalytic hydrogenation of asymmetric dynamic kinetic resolution of alpha halogenated ketone. The method has mild reaction conditions, excellent enantiomer and diastereomer selectivity, high efficiency and good yield, and has good application prospect.
Owner:SHENZHEN CATALYS SCI & TECH CO LTD
A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution
The application provides a method for constructing a planar chiral [2,2] paracyclophane by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution, which comprises the following steps: under the condition of direct current electrolysis, using a cobalt catalyst, a chiral ligand and an additive, taking a graphite felt electrode as an anode and a platinum electrode as a cathode, and allowing a racemic [2,2] paracyclophane formamide to undergo asymmetric carbon-hydrogen bond dehydrogenation coupling / kinetic resolution with an aryl acid, and after the reaction is completed, corresponding post-treatment is performed to obtain a planar chiral [2,2] paracyclophane formamide and a planar chiral oxo para-[2,2] paracyclophane. The application realizes electrochemical synthesis of the planar chiral oxo para-[2,2] paracyclophane by the method of crust-abundant transition metal catalyzed asymmetric carbon-hydrogen bond activation, the reaction substrate has wide universality, the stereoselectivity is excellent, and the product and the split-recovered raw material have excellent ee value (up to >99% ee) and a split factor (up to 1057).
![A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution](https://images-eureka.patsnap.com/patent_img/1e7e7eb1-ab91-4e94-92a9-718e66fc0e35/BDA0005198744870000031.png "A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution")
![A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution](https://images-eureka.patsnap.com/patent_img/1e7e7eb1-ab91-4e94-92a9-718e66fc0e35/BDA0005198744870000032.png "A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution")
![A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution](https://images-eureka.patsnap.com/patent_img/1e7e7eb1-ab91-4e94-92a9-718e66fc0e35/BDA0005198744870000041.png "A method for constructing facially chiral [2,2]paracyclophanes by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution")
Owner:ZHEJIANG UNIV
Asymmetric hydrogenation kinetic resolution method of racemic polysubstituted three-membered cyclic imine
PendingCN120943767AOrganic-compounds/hydrides/coordination-complexes catalystsOrganic chemistry methodsEnantiomerMetal catalyst
The invention relates to the field of asymmetric catalytic hydrogenation, in particular to an asymmetric hydrogenation kinetic resolution method of racemic polysubstituted three-membered ring imine, which is characterized by comprising the following steps: in the presence of a chiral diamine metal catalyst, carrying out asymmetric hydrogenation kinetic resolution on racemic polysubstituted three-membered ring imine; the method comprises the following steps: carrying out asymmetric hydrogenation treatment on a mixture containing enantiomers of the multi-substituted three-membered cyclic imine compound by adopting hydrogen to obtain a single optical isomer of the multi-substituted chiral aziridine compound and / or the multi-substituted chiral three-membered cyclic imine compound; wherein the polysubstituted three-membered cyclic imine compound is a compound as shown in a formula (1), and the polysubstituted chiral aziridine compound is a compound as shown in a formula (2). According to the method disclosed by the invention, the resolution of the racemic polysubstituted three-membered cyclic imine compound is realized in an asymmetric hydrogenation manner, and a polysubstituted chiral aziridine compound with certain optical purity and a single optical isomer of the polysubstituted chiral three-membered cyclic imine compound can be obtained at the same time.
Owner:INST OF CHEM CHINESE ACAD OF SCI
A method for the kinetic resolution of carbon-oxygen bonds in organocatalytic oxaspirones via hydrogenolysis.
PendingCN122079942AHigh reactivityhigh enantioselectivityOrganic compound preparationEther preparationPtru catalystPhosphate
This invention discloses a method for the kinetic resolution of oxaspirone via organocatalytic hydrogenolysis. Using chiral phosphate CPA as a catalyst, Hantzsch ester as a hydrogen source, and racemic oxaspirone 2,4-dien-6-one rac-1 as a substrate, a series of axially chiral biaryl phenolic compounds 2 are synthesized via asymmetric hydrogenolysis, and the central chiral oxaspirone 1 is recovered. This invention offers advantages such as simple and practical operation, readily available raw materials, high resolution coefficient, and good enantioselectivity. Some of the axially chiral biaryl products have structures similar to axially chiral cannabinol, possessing potential medicinal value.
Owner:DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
A method for synthesizing chiral epichlorohydrin
ActiveCN117105887BChemical recyclingOptically-active compound separationChemical industryPolymer science
The application belongs to the technical field of medicine and chemical industry, and particularly discloses a synthesis method of chiral epichlorohydrin.The chiral Salen Co(II) is in-situ oxidized, and then is reacted with TsOH or PhSO3H to obtain a catalyst Salen Co(III) OTs or Salen Co(III) SO3Ph, which is used to catalyze the asymmetric kinetic resolution of racemic epichlorohydrin and TsOH or PhSO3H at a certain temperature, and chiral epichlorohydrin is obtained at a high yield.In addition, the reaction raw material and the catalyst can be recycled and reused.
Owner:湖北楚维药业有限公司
Chiral phosphine oxide compound containing pyrrole group, preparation method and application of chiral phosphine oxide compound as antitumor drug
The invention belongs to the technical field of organic compounds, and discloses a chiral phosphine oxide compound containing a pyrrole group, a preparation method and application of the chiral phosphine oxide compound as an antitumor drug. According to the preparation method of the chiral phosphine oxide compound containing the pyrrole group, the novel P-chiral phosphine oxide compound containing the pyrrole group is constructed through [3 + 2] cycloaddition reaction of alkyne and isocyano acetate catalyzed by silver salt or cuprous salt and a chiral ligand, the reaction process is simple, the reaction condition is mild, the substrate application range is wide, and the method is suitable for industrial production. The chiral phosphine oxide containing the pyrrole group in the target product has better yield and enantioselectivity, so that the technical problems of narrower substrate application range, harsh reaction conditions and low yield of the target product in the prior art for preparing the chiral phosphine oxide by a desymmetry and kinetic resolution method are solved; meanwhile, the prepared pyrrolyl-containing phosphine oxide compound is further subjected to an anti-tumor activity test, and a relatively good tumor cell proliferation inhibition effect is shown.
Owner:SUN YAT SEN UNIV
Method for kinetic resolution of aza-aromatic hydrocarbon / chiral phosphoric acid EDA compound
The invention relates to the technical field of antiviral drugs and kinetic resolution, in particular to a method for kinetic resolution of an aza-aromatic hydrocarbon / chiral phosphoric acid EDA compound. The method specifically comprises the following steps: under visible light irradiation and a protective atmosphere, carrying out illumination reaction on a racemic nitrogen-containing heterocyclic compound shown as a formula I ', a reducing agent and a chiral phosphoric acid catalyst in an organic solvent to obtain chiral aza-arenes I and II; the method disclosed by the invention does not consider the electrical property difference of the substrate, expands the selection range of the substrate, does not participate in a photosensitizer and a transition metal catalyst, and is mild in reaction condition, high in resolution efficiency, high in atom economy and high in enantioselectivity. .
Owner:HENAN NORMAL UNIV +1
Method for obtaining 1S, 5R-pinanol through chiral carboxylic acid mediated dynamic kinetic resolution of trans-pinanol
PendingCN121293083AOrganic compound preparationCarboxylic acid esters preparationHydration reactionPtru catalyst
The invention belongs to the technical field of chiral resolution of organic compounds, and particularly discloses a method for obtaining 1S, 5R-pinanol by chiral carboxylic acid-mediated dynamic kinetic resolution of trans-pinanol, which comprises the following steps: dissolving trans-pinanol, chiral carboxylic acid and a solid acid catalyst in a solvent, stirring at a proper temperature, and reacting to obtain the 1S, 5R-pinanol. The method comprises the following steps: carrying out selective esterification reaction on trans-pinyl hydrate to generate a chiral ester intermediate, carrying out rapid racemization on unreacted trans-pinyl hydrate, after the reaction is finished, filtering and recovering a solid acid catalyst, carrying out reduced pressure rectification on filtrate, separating a product chiral ester and recovering a solvent, and further hydrolyzing the chiral ester in an alkaline system to obtain optically pure 1S, 5R-pinyl hydrate, and recovering the chiral carboxylic acid. The optically pure 1S, 5R-pinyl hydrate is prepared in a green and efficient manner by utilizing the catalytic synergistic effect of chiral carboxylic acid and solid acid, and the method has the advantages of high enantioselectivity, high raw material utilization rate, good process adaptability and good industrial application prospect.
Owner:SHANGHAI JIAOTONG UNIV +1
A method for synthesizing ferrocene-dihydroisoquinoline and ferrocene-dihydroisoquinoline planar chiral compounds
PendingCN122080089ARaw materials are easy to getlow costOptically-active compound separationMetallocenesO-Phosphoric AcidPtru catalyst
This invention discloses a method for synthesizing ferrocene-isoquinoline and ferrocene-dihydroisoquinoline planar chiral compounds, belonging to the field of asymmetric catalysis technology. Using chiral phosphoric acid (CPA) as a catalyst, 1,4-dihydropyridine compound (HEH) as a hydrogen source, and racemic ferrocene-isoquinoline derivative (+ / -)-1 and ditert-butyl dicarbonate as substrates, two types of planar chiral ferrocene compounds are synthesized through asymmetric transfer hydrogenation resolution. The enantiomeric excess of the ferrocene-isoquinoline planar chiral compounds can reach 95%, while the enantiomeric excess of the ferrocene-dihydroisoquinoline carboxylic acid tert-butyl ester planar chiral compounds can reach 89%, with a resolution coefficient (S value) reaching 50. This invention achieves the hydrogenation kinetic resolution of ferrocene-isoquinoline compounds, is simple to operate, uses commercially available catalysts, operates under mild reaction conditions, and exhibits good resolution effects, showing excellent application prospects.
Owner:DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
Alpha-methylene-gamma-butyrolactone compounds and asymmetric kinetic resolution synthesis method thereof
ActiveCN119101022BOrganic active ingredientsOrganic chemistry methodsKinetic resolutionCombinatorial chemistry
The application belongs to the technical field of medicine synthesis, and particularly relates to an alpha-methenyl-gamma-butyrolactone compound and an asymmetric kinetic resolution synthesis method thereof. The compound provided by the application is shown as formula I. The application provides a simple, efficient and alpha-methenyl-gamma-butyrolactone compound synthesis method. The series of compounds prepared have good antitumor activity and good application prospect.
Owner:SICHUAN UNIV
Application of alcohol dehydrogenase mutant in synthesis of axially chiral biaryl dimethyl carbinol
PendingCN121991908Agreen synthesisImprove substrate utilizationBacteriaMicroorganism based processesAmino acidAxial chirality
The invention relates to the technical field of biological engineering and biological catalysis, in particular to an alcohol dehydrogenase mutant and application thereof. The invention discloses an alcohol dehydrogenase mutant CpAR2-M5 (F85A / T125S / F192L / E209A / I213F). The corresponding amino acid sequence of the alcohol dehydrogenase mutant CpAR2-M5 is shown as SEQ ID No. 3. The invention also discloses a preparation method of the alcohol dehydrogenase mutant CpAR2-M5. The S-configuration axial chiral biaryl dimethyl carbinol compound can be applied to dynamic kinetic resolution asymmetric reduction of the biaryl dimethyl carbinol compound so as to prepare the S-configuration axial chiral biaryl dimethyl carbinol compound, the highest yield can reach 95%, the highest stereoselectivity can reach 99% ee, and a green, efficient and high-stereoselectivity synthesis strategy is provided for subsequent synthesis of the compound.
Owner:NANJING TECH UNIV
Carboxylesterase CarEst3 mutant and application thereof
The invention belongs to the field of biological enzyme catalysis, and provides a carboxylesterase CarEst3 mutant, the mutant is obtained by mutating phenylalanine at the 66th site of an amino acid sequence as shown in SEQ ID NO.2 into arginine, and the mutant can be used for catalyzing kinetic resolution of racemization 3-cyclohexene-1-methyl formate to prepare (S)-3-cyclohexene-1-formic acid. High stereoselectivity is achieved, and large-scale production can be achieved; the method for preparing (S)-3-cyclohexene-1-formic acid has the advantages of mild reaction conditions, high substrate concentration, good stereoselectivity, simple post-treatment, high product yield and the like.
Owner:ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD +1
Method for synthesizing chiral phthalate compounds by dynamic kinetic resolution
ActiveCN117800935BOrganic-compounds/hydrides/coordination-complexes catalystsCatalytic reactionsPtru catalystOrganic synthesis
The application discloses a method for synthesizing chiral phthalic ester compounds through dynamic kinetic resolution, and belongs to the technical field of organic synthesis. With racemic 3-hydroxy phthalic compounds 1 and anhydride 2 as raw materials, a dynamic kinetic resolution reaction is carried out under the catalysis of chiral ArPNO to obtain chiral phthalic ester compounds 3, and talosalicylate and talmetacin prodrug are synthesized. In the application, the oxygen atom in the pyridine nitrogen oxide is used as a nucleophilic site to participate in the dynamic kinetic resolution reaction, and the hydrogen in the catalyst molecule also plays a key role. The method has the advantages of mild conditions, no addition of any additive, good yield and high enantioselectivity.
Owner:HENAN NORMAL UNIV
Novel synthesis process of key intermediate (2R, 4R)-1-Boc-4-amino-2-methyl piperidinecarboxylate of Glasgabb
The invention relates to a resolution process of a key intermediate (2R, 4R)-1-Boc-4-amino-2-methyl piperidinecarboxylate of Glasgabb, and a preparation method of the key intermediate. The invention relates to a large-scale preparation method of a key intermediate (2R, 4R)-1-Boc-4-amino-2-piperidinecarboxylate of Glasgabib, which is characterized in that R-1-Boc-4-piperidinone-2-methyl formate is used as a raw material and is subjected to reductive amination at room temperature under the catalysis of a coenzyme and reductase catalytic composite catalyst, and a target product is obtained by a one-pot method. A (2R, 4R) piperidine skeleton is constructed by enzyme catalysis kinetic resolution, and the (2R, 4R) 1-Boc-4-amino-2-piperidinecarboxylate obtained by the method has the advantages that: 1, the yield is high and is increased from 41% to 95% or above; 2, the selectivity is good, the purity is high, and the ee value is more than 99%; 3, the reaction process is reasonable, the reaction conditions are mild, and the operation and post-treatment processes are simple; and 4, dangerous reaction (sodium azide is used) is avoided, the process safety is higher, and the method is suitable for industrial production. The method has the advantages of reasonable process route, simple operation and post-treatment process, cheap and easily available raw materials and low cost, and is beneficial to large-scale production.
Owner:ITIC MEDCHEM CO LTD
A method for synthesizing an r configuration axially chiral biaryl glycol mediated by alcohol dehydrogenase
The application belongs to the field of bioengineering and biocatalysis technology, and particularly relates to an alcohol dehydrogenase mutant and application thereof. The application discloses an alcohol dehydrogenase mutant CcPAR-M1 (V158L), and an amino acid sequence of the mutant is shown as SEQ ID No. 3. The mutant can be used for catalyzing asymmetric reduction reaction of a biaryl aldehyde substrate through dynamic kinetic resolution to generate R an axially chiral biaryl dimethanol compound. By using the biocatalytic system disclosed in the application, the highest yield of the target product can reach 96%, and the enantiomeric excess value can reach 99% ee at most. The method provides a green, efficient and excellent stereoselective biocatalytic strategy for construction of the axially chiral biaryl dimethanol compound.
Owner:NANJING TECH UNIV
A method for resolving racemic bodies based on dynamic dynamics
This invention discloses a method for resolving racemic mixtures based on dynamic kinetics, belonging to the field of catalysis technology. The method includes the following steps: taking a proton-selective permeable membrane and pretreating it; using the pretreated proton-selective permeable membrane to separate the aqueous phase and organic phase for reaction, thereby resolving the racemic mixture; wherein the aqueous phase is an acid solution, and the organic phase contains at least the racemic mixture, an acyl donor, an enzyme, and an organic solvent, and the racemic mixture is a racemic mixture of a chiral secondary alcohol or its derivative. This invention utilizes a proton-selective permeable membrane as a racemic catalyst applied to the dynamic kinetic resolution process, solving the problem of incompatibility between racemic catalysts and enzyme catalysts in conventional dynamic kinetic resolution techniques. This method has advantages such as a simple reaction system, easy process control, environmental friendliness, simple post-processing, and low cost.
Owner:HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
A method for preparing a chiral phthalate prodrug
ActiveCN119192108Bhigh yieldhigh enantioselectivityOrganic chemistry methodsChemical synthesisEster prodrug
The application discloses a preparation method of a chiral phthalic ester prodrug and relates to the technical field of organic chemical synthesis. In the application, isothiourea is used as a Lewis base catalyst, and acyl chloride is used as an acylating agent, so that an acylation dynamic kinetic resolution process of racemic 3-hydroxyisobenzofuran-1(3H)-one (hereinafter referred to as phthalide) is realized, thereby forming a chiral phthalic ester with good to excellent yield and enantioselectivity and natural products and drugs containing the structure.
Owner:GUIZHOU UNIV
Method for constructing surface chiral [2, 2] paracyclophane compound through activation of asymmetric carbon-hydrogen bonds under catalysis of cobalt
The invention provides a method for constructing a planar chiral [2, 2] paracyclophane compound by activating asymmetric carbon-hydrogen bonds under the catalysis of cobalt, which comprises the following steps: under the action of a cobalt catalyst and a chiral assistant, carrying out asymmetric C-H activation reaction on aryl hydrazone and racemic 4-ethynyl-[2, 2] paracyclophane, and carrying out kinetic resolution on the racemic 4-ethynyl-[2, 2] paracyclophane to obtain the planar chiral [2, 2] paracyclophane compound. After the reaction is finished, separation is carried out to obtain planar chiral 4-ethynyl-[2, 2] paracyclophane and a planar chiral 4-isoquinoline-[2, 2] paracyclophane compound; the invention further develops a research technology for catalyzing C-H activation by a cheap transition metal, and expands a synthetic strategy of the planar chiral [2, 2] paracyclophane compound; the reaction substrate is wide in adaptability, and the product is high in stereoselectivity; the multi-planar chiral [2, 2] paracyclophane compound is synthesized, the synthesis method is simple and convenient, the atom economy is good, and the synthesis efficiency is high.
![Method for constructing surface chiral [2, 2] paracyclophane compound through activation of asymmetric carbon-hydrogen bonds under catalysis of cobalt](https://images-eureka.patsnap.com/patent_img/8720e014-1a91-4f7d-905b-f2dbacf667c5/CN121974850A.png "Method for constructing surface chiral [2, 2] paracyclophane compound through activation of asymmetric carbon-hydrogen bonds under catalysis of cobalt")
Owner:ZHEJIANG UNIV
A method for synthesizing axially chiral biaryl quinoline nitroxide compounds
The application discloses a synthesis method of an axially chiral biaryl quinoline nitrogen oxygen compound and belongs to the field of organic chemistry. With racemic 1-aryl isoquinoline nitrogen oxide 1 and acrylic ester 2 as raw materials, palladium trifluoroacetate / N-acetyl-L-alanine as a catalyst, silver carbonate as an oxidant, 1,4-p-benzoquinone and trifluoroethanol as additives, asymmetric alkenylization reaction occurs in 1,2-dichloroethane / acetonitrile mixed solvents, and two types of axially chiral biaryl quinoline nitrogen oxygen compounds are obtained. The kinetic resolution method has the advantages of good resolution effect (up to 102.7), high yield and high enantioselectivity (up to 99%), and the like, and the remaining raw material can be derived through two steps to obtain a commercial (R)-QUINAP ligand.
Owner:HENAN NORMAL UNIV
Imine reductase mutant and use thereof in preparation of tofacitinib chiral amine building block
PCT designated stageWO2026031445A1BacteriaMicroorganism based processesTofacitinibMethyl palmoxirate
An imine reductase mutant and the use thereof in the preparation of a tofacitinib chiral amine building block. By means of an enzymatically coupled coenzyme regeneration system, the imine reductase mutant can efficiently catalyze racemic 1-benzyl-4-methylpiperidin-3-one as a substrate to undergo dynamic kinetic resolution and asymmetric reductive amination, so as to accurately synthesize a tofacitinib chiral amine building block (3R,4R)-1-benzyl-N-4-dimethylpiperidin-3-amine. Compared with conventional resolution methods, the technology has the significant advantages of simple operation, mild reaction conditions, environmental friendliness, high product yield, low cost, etc., and exhibits excellent application prospects in the synthesis of tofacitinib chiral amine intermediates.
Owner:EAST CHINA UNIV OF SCI & TECH
Preparation method of burkeric acid, cycloolefin copolymerization catalyst prepared from burkeric acid as well as preparation method and application of cycloolefin copolymerization catalyst
PendingCN120923512AOrganic chemistry methodsGroup 6/16 organic compounds without C-metal linkagesPolymer sciencePtru catalyst
The invention provides a preparation method of burkritic acid, a cycloolefin copolymerization catalyst prepared from burkritic acid and a preparation method and application of the cycloolefin copolymerization catalyst, and the preparation method comprises the following steps: in the presence of a nitrogen heteroatom carbene ligand, reacting a compound 1j with a compound 2 to obtain a compound 3; and hydrolyzing the compound 3 under the action of tributyltin oxide to obtain the (-)-burclalic acid. According to the synthetic route provided by the invention, by taking nitrogen heteroatom carbene as a catalyst, racemic ester is subjected to kinetic resolution, enantiomer selective ester exchange is realized, and a chiral alcohol iodization step and a chiral acyl chloride preparation step reported in literatures are simplified, so that the synthesis of the burclalic acid is simpler and more efficient, the synthesis cost is reduced, and the yield is increased. And the cost of synthesizing the ROMP catalyst is reduced. The catalyst for preparing the cycloolefin copolymer can be compounded with a cocatalyst to be used for synthesizing the cycloolefin copolymer, has higher catalytic activity and is insensitive to water and oxygen.
Owner:TOPOLEFIN TECHNOLOGY (QUZHOU) CO LTD +1
Method for synthesizing chiral phthalide derivative through dynamic kinetic resolution
The invention discloses a method for synthesizing chiral phthalide derivatives through dynamic kinetic resolution. A catalyst used in the method is a chiral diphosphine complex of palladium. According to the method, asymmetric allylation of the phthalide compound can be realized, and the high-optical-purity phthalide derivative containing continuous tertiary carbon and quaternary carbon three-dimensional centers can be obtained with excellent yield (the enantiomer excess can reach 99%, and the diastereomer proportion is up to gt; 20: 1). The method has the advantages of excellent chemical selectivity, enantioselectivity and diastereoselectivity, simple and easy operation, commercially available catalyst, mild reaction conditions, low energy consumption, environmental friendliness and high yield.
Owner:DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
Method for synthesizing axially chiral isoquinoline naphthalene compound based on nickel / light concerted catalysis
PendingCN121248500AOrganic compound preparationOrganic-compounds/hydrides/coordination-complexes catalystsChemical synthesisPtru catalyst
The invention discloses a method for synthesizing an axially chiral isoquinoline naphthalene compound based on nickel / light concerted catalysis, and belongs to the field of organic chemical synthesis. According to the present invention, the racemic isoquinoline naphthalene derivative is subjected to kinetic resolution, such that the target axial chiral isoquinoline naphthalene compound is synthesized with high yield and high enantioselectivity; according to the method, an isoquinoline naphthalene derivative and carboxylic acid are taken as raw materials and react under the action of a nickel catalyst, a chiral oxazoline ligand, a photosensitizer and alkali through visible light irradiation, so that efficient synthesis of a target product and efficient recovery of the raw materials are realized. Further, the axially chiral compound can be converted into a corresponding N-oxide catalyst through an oxidation reaction. The catalyst shows excellent catalytic activity and stereoselectivity in an asymmetric allylation reaction. The method has the advantages of mild reaction conditions, simplicity and convenience in operation, wide substrate applicability, high enantioselectivity, good atom economy and the like, and has an important industrial application prospect.
Owner:CHANGZHOU UNIV
A method for the desymmetrization of phenylmethylsulfoxide catalyzed by two enzymes
ActiveCN116064693Bachieve deracemizationImprove conversion rateOxidoreductasesFermentationCyclohexanoneCyclohexanone monooxygenase
This invention discloses a method for the deracemization of benzyl sulfoxide catalyzed by a dual-enzyme catalyst. The method includes the following steps: a) culturing and expressing genetically engineered bacteria producing cyclohexanone monooxygenase and sulfoxide reductase separately in LB medium, collecting the bacterial cells by centrifugation, and resuspending the cells in PBS buffer to obtain bacterial suspensions; b) mixing the two bacterial suspensions obtained in step a), racemic benzyl sulfoxide, DTT, and D-glucose, and reacting with shaking at 30°C; c) after the reaction is complete, extracting multiple times with an organic solvent, combining the organic phases, drying with anhydrous sodium sulfate, filtering, and recovering the solvent to obtain the target product. This invention achieves the deracemization of benzyl sulfoxide through dual-enzyme catalysis, resulting in a product with high optical purity and low raw material cost. The dynamic kinetic resolution method in aqueous solution is simple to operate, with mild reaction conditions, environmentally friendly operation, high substrate conversion rate, and good stereoselectivity.
Owner:GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY
D-amino acid oxidase mutant and use thereof
The present invention relates to the technical field of biology and in particular to a D-amino acid oxidase mutant and a use thereof in the preparation of L-glufosinate by kinetic resolution of DL-glufosinate and the multi-enzyme catalysis. By means of methods such as protein truncation, multi-site combination mutation, and fusion tag addition, the soluble expression and enzymatic activity of D-amino acid oxidase obtained by means of expression in a host are significantly improved. Further modification of an active pocket of the D-amino acid oxidase provides a variety of amino acid oxidase mutants capable of efficiently catalyzing the synthesis of 2-oxo-4-(hydroxymethylphosphinyl) butyric acid (PPO) from D-glufosinate, such that the enzymatic activity of the D-amino acid oxidase is further improved. A method for preparing an α-keto acid by using the provided D-amino acid oxidase achieves the kinetic resolution of racemic glufosinate and can be widely applied to the production of L-glufosinate.
Owner:ZHEJIANG XINAN CHEM IND GRP CO LTD +1
Method for synthesizing chiral fluorine-containing quaternary carbon unsaturated ketone through ruthenium catalytic transfer hydrogenation kinetic resolution
PendingCN121378001AOrganic compound preparationOrganic-compounds/hydrides/coordination-complexes catalystsPtru catalystKinetic resolution
The invention discloses a method for synthesizing chiral fluorine-containing quaternary carbon unsaturated ketone through ruthenium catalytic transfer hydrogenation kinetic resolution, the fluorine-containing quaternary carbon unsaturated ketone is used as a reaction substrate 1, a chiral dinitrogen ligand of ruthenium is used as a catalyst, the chiral fluorine-containing quaternary carbon unsaturated ketone 1 'is synthesized through asymmetric transfer hydrogenation kinetic resolution, and the selectivity factor can reach 214.4. The method is simple and practical to operate, excellent in enantioselectivity and diastereoselectivity and wide in substrate range, and the reaction is green, atom-economical and environment-friendly.
Owner:UNIV OF SCI & TECH OF CHINA +1
A method for the synthesis of a florfenicol key intermediate
The application provides a synthesis method of a key intermediate of florfenicol, and particularly relates to a preparation method of (1R,2R)-2-amino-1-(4-methylsulfonyl)phenyl-1,3-propanediol. The application utilizes the selectivity of ketoreductase to the substrate carbonyl ortho position chirality, realizes dynamic kinetic resolution (DKR) while reducing the carbonyl group to obtain a pure chiral compound, and then reduces the chiral compound to obtain a target product. The method is simple in process, high in selectivity, and greatly improves the product yield.
Owner:ANHUI LIBO PHARMACEUTICAL CO LTD