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
收藏
页码：579 / 585
页数：7
相关论文
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
    BOSTMEMBRUNDESRUT, M
    DAUPHIN, G
    KERGOMARD, A
    RENARD, MF
    VESCHAMBRE, H
    [J]. 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
    BUISSON, D
    AZERAD, R
    SANNER, C
    LARCHEVEQUE, M
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (10) : 987 - 988
  • [4] Preparation and use of (S)-O-acetyllactyl chloride (Mosandl's reagent) as a chiral derivatizing agent
    Buisson, D
    Azerad, R
    [J]. 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
    CANET, I
    COURTIEU, J
    DAUPHIN, G
    GOURCY, JG
    VESCHAMBRE, H
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 333 - 336
  • [7] RING-OPENING OF CYCLOPROPYLKETONES INDUCED BY PHOTOCHEMICAL ELECTRON-TRANSFER
    COSSY, J
    FURET, N
    BOUZBOUZ, S
    [J]. TETRAHEDRON, 1995, 51 (43) : 11751 - 11764
  • [8] MICROBIOLOGICAL REDUCTION OF ALPHA,BETA-ETHYLENIC ALDEHYDES BY BEAUVERIA-SULFURESCENS
    DESRUT, M
    KERGOMARD, A
    RENARD, MF
    VESCHAMBRE, H
    [J]. 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
    FAUVE, A
    RENARD, MF
    VESCHAMBRE, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) : 4893 - 4897
123