Chemoenzymatic synthesis of enantiopure isopropyl (3R)- and (3S)-3-hydroxycyclohex-1-ene-1-carboxylates and their reduction to isomers of isopropyl 3-hydroxy-cyclohexane-1-carboxylate

被引：7

作者：

Fonteneau, L ^{[1
]}

Rosa, S ^{[1
]}

Buisson, D ^{[1
]}

机构：

[1] Univ Paris 05, Chim & Biochim Pharmacol & Toxicol Lab, CNRS, UMR 8601, F-75270 Paris 06, France

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(02)00152-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reduction of an alpha,beta-unsaturated cyclic ketone with Geotrichum candidum affords the corresponding (S)-allylic alcohol, while enantiospecific oxidation of the corresponding racemic alcohols leases the (R)-enantiomer unchanged, giving access to both enantiomeric forms. Subsequent chemical reduction of the double bond of these homochiral allylic alcohol allows all isomers of the corresponding cyclohexanols to be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：579 / 585

页数：7

共 22 条

[1] REDUCTION OF 1,1-DIDEUTERIO-2-METHYL-2-PENTEN-1-OL BY BEAUVERIA-SULFURESCENS - MECHANISM OF THE MICROBIOLOGICAL REDUCTION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND ALCOHOLS [J].

BOSTMEMBRUNDESRUT, M ;

DAUPHIN, G ;

KERGOMARD, A ;

RENARD, MF ;

VESCHAMBRE, H .

TETRAHEDRON, 1985, 41 (18) :3679-3682

[2]

Buisson D., 1992, Biocatalysis, V5, P249, DOI 10.3109/10242429209014871

[3] STEREOCONTROLLED REDUCTION OF BETA-KETOESTERS BY GEOTRICHUM-CANDIDUM - PREPARATION OF D-3-HYDROXYALKANOATES [J].

BUISSON, D ;

AZERAD, R ;

SANNER, C ;

LARCHEVEQUE, M .

TETRAHEDRON-ASYMMETRY, 1991, 2 (10) :987-988

[4] Preparation and use of (S)-O-acetyllactyl chloride (Mosandl's reagent) as a chiral derivatizing agent [J].

Buisson, D ;

Azerad, R .

TETRAHEDRON-ASYMMETRY, 1999, 10 (15) :2997-3002

[5]

Buisson D., 1990, BIOCATALYSIS, V3, P85

[6] ENANTIOMERIC EXCESS ANALYSIS OF (2R, 3S)-3-DEUTERIO-2-METHYLCYCLOHEXANONE AND (1S, 2R, 3S)-3-DEUTERIO-2-METHYLCYCLOHEXANOL, THROUGH DEUTERIUM NMR IN A POLYPEPTIDE LYOTROPIC LIQUID-CRYSTAL [J].

CANET, I ;

COURTIEU, J ;

DAUPHIN, G ;

GOURCY, JG ;

VESCHAMBRE, H .

TETRAHEDRON-ASYMMETRY, 1995, 6 (02) :333-336

[7] RING-OPENING OF CYCLOPROPYLKETONES INDUCED BY PHOTOCHEMICAL ELECTRON-TRANSFER [J].

COSSY, J ;

FURET, N ;

BOUZBOUZ, S .

TETRAHEDRON, 1995, 51 (43) :11751-11764

[8] MICROBIOLOGICAL REDUCTION OF ALPHA,BETA-ETHYLENIC ALDEHYDES BY BEAUVERIA-SULFURESCENS [J].

DESRUT, M ;

KERGOMARD, A ;

RENARD, MF ;

VESCHAMBRE, H .

TETRAHEDRON, 1981, 37 (22) :3825-3829

[9]

FABER K, 1995, BIOTRANSFORMATIONS O, P168

[10] INDUCIBILITY OF AN ENONE REDUCTASE SYSTEM IN THE FUNGUS BEAUVERIA-SULFURESCENS - APPLICATION IN ENANTIOSELECTIVE ORGANIC-SYNTHESIS [J].

FAUVE, A ;

RENARD, MF ;

VESCHAMBRE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4893-4897

← 1 2 3 →