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.
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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 [J].
ARMANI, E ;
DOSSENA, A ;
MARCHELLI, R ;
CASNATI, G .
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 [J].
BESSE, P ;
VESCHAMBRE, H .
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 [J].
CABON, O ;
LARCHEVEQUE, M ;
BUISSON, D ;
AZERAD, R .
TETRAHEDRON LETTERS, 1992, 33 (48) :7337-7340
[7]  
CARPY A, IN PRESS J MOL STRUC
[8]   BAKERS-YEAST REDUCTION OF ALPHA-HALOACETOPHENONES [J].
DECARVALHO, M ;
OKAMOTO, MT ;
MORAN, PJS ;
RODRIGUES, JAR .
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 [J].
GOLDING, BT ;
HALL, DR ;
SAKRIKAR, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (11) :1214-1220