[go: up one dir, main page]

Sanchez et al., 1999 - Google Patents

Candida a ntarctica Lipase-Catalyzed Doubly Enantioselective Aminolysis Reactions. Chemoenzymatic Synthesis of 3-Hydroxypyrrolidines and 4-(Silyloxy)-2 …

Sanchez et al., 1999

Document ID
11935316570892894791
Author
Sanchez V
Rebolledo F
Gotor V
Publication year
Publication venue
The Journal of Organic Chemistry

External Links

Snippet

Aminolyses of racemic and prochiral 3-hydroxyesters with racemic amines are effectively catalyzed by Candida antarctica lipase. In these processes, the simultaneous resolution of the ester and the amine, or the corresponding asymmetrization− resolution, takes place. In …
Continue reading at pubs.acs.org (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
    • C12P41/007—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or micro-organisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members

Similar Documents

Publication Publication Date Title
Sanchez et al. Candida a ntarctica Lipase-Catalyzed Doubly Enantioselective Aminolysis Reactions. Chemoenzymatic Synthesis of 3-Hydroxypyrrolidines and 4-(Silyloxy)-2-oxopyrrolidines with Two Stereogenic Centers
Träff et al. A chemoenzymatic dynamic kinetic resolution approach to enantiomerically pure (R)-and (S)-duloxetine
Tang et al. Dynamic kinetic resolution via dual-function catalysis of modified cinchona alkaloids: Asymmetric synthesis of α-hydroxy carboxylic acids
Gastaldi et al. Dynamic kinetic resolution of amines involving biocatalysis and in situ free radical mediated racemization
van der Deen et al. Lipase-Catalyzed Second-Order Asymmetric Transformations as Resolution and Synthesis Strategies for Chiral 5-(Acyloxy)-2 (5 H)-Furanone and Pyrrolinone Synthons
Li et al. Preparation of (R)-and (S)-N-protected 3-hydroxypyrrolidines by hydroxylation with Sphingomonas sp. HXN-200, a highly active, regio-and stereoselective, and easy to handle biocatalyst
Mangas-Sanchez et al. Chemoenzymatic synthesis of rivastigmine based on lipase-catalyzed processes
Puertas et al. Enantioselective enzymatic aminolysis and ammonolysis of dimethyl 3-hydroxyglutarate. Synthesis of (R)-4-amino-3-hydroxybutanoic acid
Yoshimitsu et al. Synthesis of (−)-Muricatacin via α-and α ‘-C− H Bond Functionalization of Tetrahydrofuran
Martín-Matute et al. Ruthenium-and enzyme-catalyzed dynamic kinetic asymmetric transformation of 1, 4-diols: Synthesis of γ-hydroxy ketones
Chang et al. Preparation of (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones by regio-and stereoselective hydroxylation with Sphingomonas sp. HXN-200
Berkessel et al. Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β2‐Amino Acids
Fransson et al. Kinetic resolution and chemoenzymatic dynamic kinetic resolution of functionalized γ-hydroxy amides
Limanto et al. An efficient chemoenzymatic approach to (S)-γ-fluoroleucine ethyl ester
Kato et al. Microbial deracemization of α-substituted carboxylic acids
Goswami et al. Enzymatic desymmetrization of dimethyl cylcohex-4-ene-cis-1, 2-dicarboxylate to (1 S, 2 R)-2-(methoxycarbonyl) cyclohex-4-ene-1-carboxylic acid
Dehli et al. Dynamic kinetic resolution of 2-oxocycloalkanecarbonitriles: Chemoenzymatic syntheses of optically active cyclic β-and γ-amino alcohols
Purkarthofer et al. Large-scale synthesis of (R)-2-amino-1-(2-furyl) ethanol via a chemoenzymatic approach
Chang et al. Enantioselective Trans dihydroxylation of nonactivated C− C double bonds of aliphatic heterocycles with Sphingomonas sp. HXN-200
Cuiper et al. Kinetic resolutions and enantioselective transformations of 5-(acyloxy) pyrrolinones using Candida antarctica lipase B: synthetic and structural aspects
Antolini et al. Stereoselective synthesis of erythro β-substituted aspartates
Dehli et al. Preparation of enantiopure ketones and alcohols containing a quaternary stereocenter through parallel kinetic resolution of β-keto nitriles
de Gonzalo et al. Anhydrides as acylating agents in the enzymatic resolution of an intermediate of (−)-paroxetine
Solares et al. Enzymatic resolution of a quaternary stereogenic centre as the key step in the synthesis of (S)-(+)-citalopram
López-García et al. Synthesis of (R)-3, 4-diaminobutanoic acid by desymmetrization of dimethyl 3-(benzylamino) glutarate through enzymatic ammonolysis