SUBSTITUENT EFFECT ON THE ABSOLUTE STEREOCHEMISTRY OF THE ASYMMETRIC REDUCTION OF FLUORINE-CONTAINING BETA-DIKETONES BY BAKERS-YEAST

被引:8
作者
BUCCIARELLI, M [1 ]
FORNI, A [1 ]
MORETTI, I [1 ]
PRATI, F [1 ]
TORRE, G [1 ]
机构
[1] UNIV MODENA,DIPARTIMENTO CHIM,VIA CAMPI 183,I-41100 MODENA,ITALY
来源
BIOCATALYSIS | 1994年 / 9卷 / 1-4期
关键词
BAKERS YEAST REDUCTION; CHIRAL FLUORINATED BETA-HYDROXYKETONES; ABSOLUTE CONFIGURATION;
D O I
10.3109/10242429408992130
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Fluorine-containing beta-diketones (1a-d) were reduced by free bakers' yeast (FBY) and immobilized baker yeast (IMBY) in water, to give optically-active fluorinated beta-hydroxyketones (2a-d). It was found that the reaction is highly regioselective, and that the stereochemistry of the reduction is controlled by the R substituent.
引用
收藏
页码:313 / 320
页数:8
相关论文
共 9 条
[1]  
BOLTE J, 1986, TETRAHEDRON LETT, V27, P5565
[2]  
BOLTE J, 1993, PREPARATIVE BIOTRANS
[3]  
BUCCIARELLI M, 1990, GAZZ CHIM ITAL, V120, P99
[4]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[5]   USE OF BIOLOGICAL-SYSTEMS FOR THE SYNTHESIS OF CHIRAL MOLECULES .5. MICROBIOLOGICAL REDUCTION OF ACYCLIC BETA-DIKETONES [J].
FAUVE, A ;
VESCHAMBRE, H .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22) :5215-5219
[6]  
KIKKAWA I, 1980, SYNTHESIS-STUTTGART, P877
[7]   HIGHLY ENANTIOSELECTIVE REDUCTION OF ETHYL 2-ACYLOXY-3-OXOBUTANOATE WITH IMMOBILIZED BAKERS-YEAST [J].
SAKAI, T ;
NAKAMURA, T ;
FUKUDA, K ;
AMANO, E ;
UTAKA, M ;
TAKEDA, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (10) :3185-3188
[8]   PREPARATION BY YEAST REDUCTION AND DETERMINATION OF THE SENSE OF CHIRALITY OF ENANTIOMERICALLY PURE ETHYL (-)-4,4,4-TRICHLORO-3-HYDROXYBUTANOATE AND (+)-4,4,4-TRIFLUORO-3-HYDROXYBUTANOATE [J].
SEEBACH, D ;
RENAUD, P ;
SCHWEIZER, WB ;
ZUGER, MF ;
BRIENNE, MJ .
HELVETICA CHIMICA ACTA, 1984, 67 (07) :1843-1853
[9]  
TAIN LJ, 1987, J ORG CHEM, V52, P3211