CHEMOENZYMATIC SYNTHESIS OF CHIRAL EPOXIDES - PREPARATION OF 4-PHENYL-2,3-EPOXYBUTANE AND 1-PHENYL-1,2-EPOXYPROPANE

被引:26
作者
BESSE, P [1 ]
RENARD, MF [1 ]
VESCHAMBRE, H [1 ]
机构
[1] UNIV CLERMONT FERRAND,CHIM ORGAN BIOL LAB,CNRS,URA 485,F-63177 CLERMONT FERRAND,FRANCE
关键词
D O I
10.1016/0957-4166(94)80167-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.
引用
收藏
页码:1249 / 1268
页数:20
相关论文
共 19 条
  • [1] REACTION OF ALDEHYDES AND KETONES WITH TERT-BUTYL BROMIDE-DIMETHYL SULFOXIDE
    ARMANI, E
    DOSSENA, A
    MARCHELLI, R
    CASNATI, G
    [J]. TETRAHEDRON, 1984, 40 (11) : 2035 - 2039
  • [2] ARMSTRONG VW, 1975, TETRAHEDRON LETT, P373
  • [3] BELRHLID R, 1992, BIOCATALYSIS, V6, P319
  • [4] CHEMOENZYMATIC SYNTHESIS OF ALPHA-BICHIRAL SYNTHONS - APPLICATION TO THE PREPARATION OF CHIRAL EPOXIDES
    BESSE, P
    VESCHAMBRE, H
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (06) : 1271 - 1285
  • [5] BODOT H, 1960, B SOC CHIM FR, P1086
  • [6] MICROBIAL REDUCTION OF 2-CHLORO-3-ARYL-3-OXOPROPIONIC ACID-ESTERS
    CABON, O
    LARCHEVEQUE, M
    BUISSON, D
    AZERAD, R
    [J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7337 - 7340
  • [7] CARPY A, IN PRESS J MOL STRUC
  • [8] BAKERS-YEAST REDUCTION OF ALPHA-HALOACETOPHENONES
    DECARVALHO, M
    OKAMOTO, MT
    MORAN, PJS
    RODRIGUES, JAR
    [J]. TETRAHEDRON, 1991, 47 (12-13) : 2073 - 2080
  • [9] Fauve A., 1990, BIOCATALYSIS, V3, P95
  • [10] REACTION BETWEEN VICINAL DIOLS AND HYDROGEN BROMIDE IN ACETIC-ACID - SYNTHESIS OF CHIRAL PROPYLENE-OXIDE
    GOLDING, BT
    HALL, DR
    SAKRIKAR, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (11): : 1214 - 1220