The stereoselective preparation of beta-hydroxy esters using a yeast reduction in an organic solvent

被引:60
作者
Medson, C [1 ]
Smallridge, AJ [1 ]
Trewhella, MA [1 ]
机构
[1] VICTORIA UNIV TECHNOL,DEPT BIOL & CHEM,MELBOURNE,VIC 8001,AUSTRALIA
关键词
D O I
10.1016/S0957-4166(97)00050-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A range of (S)-beta-hydroxy esters has been prepared in high yield (56-96%) and with very high enantioselectivity (>94%) using a yeast mediated reduction in light petroleum. It was found that the ester functionality had a marked effect on both the isolated yield and the quantity of yeast required to effect complete reduction. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1049 / 1054
页数:6
相关论文
共 22 条
[1]   The yeast-mediated reduction of nitrostyrenes in organic solvent systems [J].
Bak, RR ;
McAnda, AF ;
Smallridge, AJ ;
Trewhella, MA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1996, 49 (11) :1257-1260
[2]   THE REACTIONS OF DIKETENE WITH KETONES [J].
CARROLL, MF ;
BADER, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (21) :5400-5402
[3]   BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].
CSUK, R ;
GLANZER, BI .
CHEMICAL REVIEWS, 1991, 91 (01) :49-97
[4]   YEAST-MEDIATED RESOLUTION OF BETA-KETO-ESTERS OF PROCHIRAL ALCOHOLS [J].
HUDLICKY, T ;
TSUNODA, T ;
GADAMASETTI, KG ;
MURRY, JA ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) :3619-3623
[5]   THE USE OF ORGANIC-SOLVENT SYSTEMS IN THE YEAST MEDIATED REDUCTION OF ETHYL ACETOACETATE [J].
JAYASINGHE, LY ;
KODITUWAKKU, D ;
SMALLRIDGE, AJ ;
TREWHELLA, MA .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (09) :2528-2531
[6]   C45-CAROTENOID AND C50-CAROTENOID .1. SYNTHESIS OF (R)-LAVANDULOL AND (S)-LAVANDULOL [J].
KRAMER, A ;
PFANDER, H .
HELVETICA CHIMICA ACTA, 1982, 65 (01) :293-301
[7]  
LAWESSON SO, 1973, ORG SYNTH, V5, P155
[8]   BIOCHEMISTRY OF THE USTILAGINALES .4. THE CONFIGURATIONS OF SOME BETA-HYDROXYACIDS AND THE BIOREDUCTION OF BETA-KETOACIDS [J].
LEMIEUX, RU ;
GIGUERE, J .
CANADIAN JOURNAL OF CHEMISTRY, 1951, 29 (08) :678-690
[9]  
Levene PA, 1926, J BIOL CHEM, V69, P165
[10]   SYNTHESIS OF OPTICALLY-ACTIVE PHEROMONES [J].
MORI, K .
TETRAHEDRON, 1989, 45 (11) :3233-3298