Asymmetric hydrolysis of pro-chiral 3,3-disubstituted 2,4-diacetoxycyclohexa-1,4-dienes

被引:16
作者
Renouf, P
Poirier, JM
Duhamel, P
机构
[1] UNIV ROUEN,FAC SCI,CNRS,URA 464,F-76821 MONT ST AIGNAN,FRANCE
[2] UNIV ROUEN,IRCOF,F-76821 MONT ST AIGNAN,FRANCE
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 11期
关键词
D O I
10.1039/a606001c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric enzymatic hydrolysis of pro-chiral 3,3-disubstituted 2,4-diacetoxycyclohexa-1,4-dienes 2 affords in high yields optically pure 2,2-disubstituted 3-acetoxycyclohex-3-enones 1 (>98% ee). Under mild conditions Candida cylindracea lipase (enzyme/substrate ratio = 2%) hydrolyses specifically the pro-S enol ester function of the pro-chiral starting material 2.
引用
收藏
页码:1739 / 1745
页数:7
相关论文
共 24 条
[1]  
ABRAMOWICZ DA, 1990, BIOCATALYSIS
[2]  
AZERAD R, 1995, B SOC CHIM FR, V132, P17
[3]   ASYMMETRIC MICROBIAL REDUCTION OF PROCHIRAL 2,2-DISUBSTITUTED CYCLOALKANEDIONES [J].
BROOKS, DW ;
MAZDIYASNI, H ;
GROTHAUS, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3223-3232
[4]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[5]  
DAVIES HG, 1989, BIOTRANSFORMATIONS P
[6]   UNPRECEDENTED ROUTE TO ENOLATES FROM SILYL ENOL ETHERS AND ENOL ACETATES - REACTION WITH HARD AND SOFT ELECTROPHILES [J].
DUHAMEL, P ;
CAHARD, D ;
POIRIER, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (21) :2509-2511
[7]   ASYMMETRIC-SYNTHESIS BY ENZYMATIC-HYDROLYSIS OF PROCHIRAL DIENOL DIACETATE [J].
DUHAMEL, P ;
RENOUF, P ;
CAHARD, D ;
YEBGA, A ;
POIRIER, JM .
TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2447-2450
[8]   CHEMISTRY OF CARBANIONS .18. PREPARATION OF TRIMETHYLSILYL ENOL ETHERS [J].
HOUSE, HO ;
CZUBA, LJ ;
GALL, M ;
OLMSTEAD, HD .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08) :2324-&
[9]   ENZYMES IN ORGANIC-SYNTHESIS [J].
JONES, JB .
TETRAHEDRON, 1986, 42 (13) :3351-3403
[10]  
JONES JB, 1976, APPL BIOCH SYSTEMS O