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56 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.
Mutant, expression vector, host and application thereof
The invention relates to the field of bioengineering, in particular to a mutant, an expression vector, a host and application thereof. The invention provides application of a mutation site as a target spot in preparation of alpha keto acid and / or L-glufosinate-ammonium. The mutation sites comprise one or more of the 52nd site, the 54th site, the 56th site, the 58th site, the 217th site, the 354th site and the 355th site of the D-amino acid oxidase. According to the invention, an active pocket of D-amino acid oxidase is modified, and a D-amino acid oxidase single-point or multi-point combined mutant with significantly enhanced catalytic activity on a catalytic substrate DL-glufosinate-ammonium is screened through multiple rounds of iterative saturated mutation. By utilizing the D-amino acid oxidase mutant provided by the invention, kinetic resolution of racemic glufosinate-ammonium is realized, and the D-amino acid oxidase mutant can be widely applied to production and application of L-glufosinate-ammonium.
Owner:ZHEJIANG XINAN CHEM IND GRP CO LTD +1
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
Kinetic resolution method for asymmetric catalytic hydrogenation of racemic beta-aryl ester or lactone
PendingCN120423934AOrganic compound preparationOrganic-compounds/hydrides/coordination-complexes catalystsPtru catalystTurnover number
The invention provides a kinetic resolution method for asymmetric catalytic hydrogenation of racemic beta-aryl ester or lactone. Specifically, the invention provides a kinetic resolution method for asymmetric catalytic hydrogenation of racemic beta-aryl ester or lactone containing aryl, alkenyl, alkynyl and alkyl, and chiral gamma-aryl primary alcohol is prepared. According to the method, a chiral Ir-SpiroPAP catalyst or an enantiomer thereof is adopted, and the conversion number of the chiral Ir-SpiroPAP catalyst is as high as 600. In the imgabs0 #, R can be aryl, substituted aryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkyl or cyclic alkyl; r2 is alkyl; x can be hydrogen, alkyl, alkoxy, halogen or carboxylic ester group; wherein the structural formula of the Ir-SpiroPAP catalyst is # imgabs 1 # or an enantiomer thereof, and Y is hydrogen or alkyl.
Owner:JIUZHOU PHARMACEUTICAL (HANGZHOU) CO LTD
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
Chiral 6-NH2 uracil compound as well as preparation method and application thereof
PendingCN120097923AOrganic active ingredientsOrganic chemistry methodsChemical synthesisO-Phosphoric Acid
The invention discloses a chiral 6-NH2 uracil compound as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The invention provides a method for constructing C-N axial chiral 6-NH2 uracil and a corresponding amide compound thereof through asymmetric organic catalysis, under the catalysis of chiral phosphoric acid, racemization 6-NH2 uracil and azlactone are used as reaction substrates, and 6-amide uracil with optical activity is obtained by utilizing a kinetic resolution strategy. And the 6-NH2 uracil compound with optical activity is recovered. According to the method, chiral uracil is constructed by using an asymmetric catalysis strategy for the first time, and the method has the characteristics of convenience in operation, cheap and easily available raw materials, and high yield and enantioselectivity. The C-N axial chiral uracil shows excellent anti-tumor cell activity, and especially has excellent biological activity on colon cancer, cervical cancer, multiple myeloma, prostate cancer cells and the like.
Owner:SICHUAN UNIV
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
A method for synthesizing chiral flavanol compounds by dynamic kinetic resolution
The present invention discloses a method for asymmetric transfer hydrogenation synthesis of chiral flavanol compounds by dynamic kinetic resolution, and the catalyst used is a chiral ruthenium diamine complex. Through this method, asymmetric transfer hydrogenation of flavanone derivatives can be realized, and optically pure flavanol compounds containing three consecutive chiral centers can be obtained in high yield (the enantiomeric excess can reach 99%, and the diastereomeric ratio can reach >20:1). The present invention has high enantioselectivity and diastereoselectivity, is simple and easy to operate, the catalyst is commercially available, the reaction conditions are mild, the energy consumption is low, it is environmentally friendly and has good yield, and gram-scale experiments can be realized without loss of activity and enantioselectivity.
Owner:DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
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
Method for preparing L-navidine through kinetic resolution
PendingCN120349324AOptically-active compound separationOrganic racemisationPtru catalystPhenethylamine derivative
The invention discloses a method for preparing levo-nalvidine by kinetic resolution, which comprises the following steps: adding racemic nalvidine and a proper amount of chiral resolution catalyst into a reaction container, then adding a mixed solvent formed by alcohol and organic amine, and stirring the whole reaction system at 60-80 DEG C until a clear solution is formed; immediately cooling to 30-50 DEG C, and then preserving heat for 24-72 hours; cooling to room temperature, continuously stirring for 1-3 hours at room temperature, filtering, leaching the obtained solid with a mixed solvent, and drying at room temperature; the chiral resolution catalyst is a chiral phenylethylamine derivative and is selected from any one compound in the following structural formula: # imgabs0 #. According to the method, the high-optical-purity levo-nalvidine can be obtained at high yield by adopting a simple operation process under a mild condition, and the chiral resolution catalyst is low in cost, easy to obtain, suitable for large-scale application and suitable for industrial production. The method has an important value for realizing large-scale production of L-galanthamine.
Owner:EAST CHINA UNIV OF SCI & TECH
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
An enantiopure planar chiral dibenzodiazocinone compound, its preparation method and applications
ActiveCN116947768BAmino compound purification/separationOrganic chemistry methodsKinetic resolutionAcyl group
The present invention discloses an enantiopure planar chiral dibenzo diazocin dione compound, which has the characteristics of novel structure and provides a novel skeleton for planar chiral compounds. The present invention also provides a preparation method of the above compound. This planar chiral compound can be obtained by catalytic asymmetric kinetic resolution of readily available racemic dibenzo diazocin dione. The operation is simple and the structure is easy to modify. The present invention further provides the application of the above compound. This planar chiral compound is used as a chiral acylation reagent to resolve racemic 3,3-dimethylbutan-2-amine. The reaction conditions are mild, the yield is high, and the enantioselectivity is moderate.
Owner:ZHENGZHOU UNIV
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
Synthetic method of isotactic polythioester and chiral 2-substituted mercaptopropionic acid
The invention relates to the field of synthesis of chiral polymers and chiral small organic molecules, in particular to a preparation method of a racemic 3-substituted-2-ketothiolactone monomer. The invention relates to a method for preparing isotactic thiolactone through kinetic resolution ring-separation polymerization reaction and a method for preparing an optically pure 3-substituted-2-ketothiolactone monomer. A process for preparing optically pure polymers by ring-opening polymerization; the invention relates to a method for preparing optically pure 2-substituted thiohydracrylic acid serving as a drug synthesis intermediate from optically pure 3-substituted-2-ketothiolactone.
Owner:SICHUAN UNIV
Chiral synthesis method of (S)-sulconazole
The invention discloses a kinetic resolution method of terminal N-carbamate aziridine and a chiral synthesis method of (S)-baclofen and (S)-sulconazole, and belongs to the technical field of chiral synthesis. The method comprises the step of obtaining one enantiomer product with a high ee (enantiomeric excess) value by adopting a terminal N-carbamate aziridine raceme as a reaction raw material under the action of a catalyst. The kinetic resolution method of the terminal N-carbamate aziridine has the advantages that the applicable aziridine substrate range is wide, the chiral recognition capability is high, and the method has a wide application prospect in the field of chiral resolution or chiral synthesis.
Owner:SHANDONG 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
Application of asymmetric catalytic hydrogenation kinetic resolution method of racemic beta-aryl ester or lactone in synthesis of chiral drugs and natural products
The invention provides an application of a kinetic resolution method for asymmetric catalytic hydrogenation of racemic beta-aryl ester or lactone. According to the method, a chiral Ir-SpiroPAP catalyst is adopted, and obtained chiral gamma-aryl primary alcohol and chiral beta-aryl ester serve as key chiral raw materials to be used for selective enantiomer synthesis of oligomers of tolterodine, methoxydalaninone, AM-1638, AMG-837, fusterodine, enrasentan and resveratrol, and the chiral gamma-aryl primary alcohol and the chiral beta-aryl ester are used for selective enantiomer synthesis of the oligomers of the tolterodine, the methoxydalaninone, the AM-1638, the AMG-837, the fusterodine, the enrasentan and the resveratrol.
Owner:JIUZHOU PHARMACEUTICAL (HANGZHOU) 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
C2 symmetric N-N axial chiral biindolyl diphosphine ligand as well as preparation method and application thereof
PendingCN119930684AOrganic compound preparationOrganic-compounds/hydrides/coordination-complexes catalystsOrganic synthesisHalocarbon
The invention belongs to the technical field of organic synthetic chemistry, and particularly relates to a C2 symmetric N-N axial chiral biindolyl diphosphine ligand as well as a preparation method and application thereof. The preparation method comprises the following steps: reacting 2-indolyl amino aryl benzaldehyde or 2-indolyl amino aryl benzophenone with carbon tetrahalide to generate a 1, 1-dihalogenated olefin compound 3; carrying out cyclization reaction on the 1, 1-dihalogenated olefin compound 3 under the action of transition metal to obtain a biindole compound 4; reacting the biindole halide 4 with diaryl phosphorus halide in the presence of alkyl metal to generate a biindole diaryl phosphine compound 5; and reacting the biindolyl diaryl phosphine compound 5 with diaryl phosphorus halide in the presence of alkyl metal to generate the compound as shown in the general formula I. The optical pure chiral diphosphine ligand can be obtained through kinetic resolution, chiral preparative column separation and other methods. The ligand is simple in framework, convenient to synthesize and easy to transform, can be applied to asymmetric reactions catalyzed by various metals, and has very high reaction activity and stereoselectivity.
Owner:QINGDAO UNIV
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
A method for the synthesis of axially chiral biaryl compounds by palladium-catalyzed asymmetric hydrogenolysis
The present invention discloses a method for palladium-catalyzed asymmetric hydrogenolysis to synthesize axially chiral biaryl compounds, which realizes the palladium-catalyzed asymmetric hydrogenolysis of aryl trifluoromethanesulfonates through kinetic resolution, thereby enabling the facile construction of a series of axially chiral biaryl compounds with excellent selectivity factors (the highest s value reaches 70). Additionally, some chiral monophosphine ligands were prepared from these axially chiral biaryl compounds as raw materials and applied to palladium-catalyzed asymmetric allylic alkylation reactions, obtaining products of allylic alkylation with excellent enantioselectivity and regioselectivity, demonstrating the potential utility of this method. The method of the present invention is simple, practical, the catalyst is commercially available, the reaction conditions are mild, the energy consumption is low, and it is environmentally friendly.
Owner:DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES