Bioreduction of 2-oxocyclopentanecarboxamides:: syntheses of optically active 2-aminomethyl- and 2-aminocyclopentanols

被引:18
作者
Quirós, M [1 ]
Rebolledo, F [1 ]
Gotor, V [1 ]
机构
[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
关键词
D O I
10.1016/S0957-4166(99)00016-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The fungus Mortierella isabellina NRRL 1757 catalyzes the reduction of 2-oxocyclopentanecarboxamides with very high enantioselectivity giving, in most cases, the corresponding enantiopure 2-hydroxycyclopentanecarboxamides. The presence or absence of a substituent on the amidic nitrogen has a strong influence on the diastereoselectivity achieved in these processes. Optically active hydroxyamides prepared in these microbial reductions are used as starting materials for the preparation of optically active 2-aminomethyl- and 2-aminocyclopentanols. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:473 / 486
页数:14
相关论文
共 49 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]  
[Anonymous], NMR SPECTROSCOPY BAS
[3]  
BERNATH G, 1989, HUNG TELIES HU, V48, P865
[4]   CHEMOENZYMATIC SYNTHESIS OF CHIRAL BETA-AZIDOALCOHOLS - APPLICATION TO THE PREPARATION OF CHIRAL AZIRIDINES AND AMINOALCOHOLS [J].
BESSE, P ;
VESCHAMBRE, H ;
CHENEVERT, R ;
DICKMAN, M .
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1727-1744
[5]   CHIRALITY EMERGES AS KEY ISSUE IN PHARMACEUTICAL RESEARCH [J].
BORMAN, S .
CHEMICAL & ENGINEERING NEWS, 1990, 68 (28) :9-14
[6]   REDUCTION OF 1,1-DIDEUTERIO-2-METHYL-2-PENTEN-1-OL BY BEAUVERIA-SULFURESCENS - MECHANISM OF THE MICROBIOLOGICAL REDUCTION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND ALCOHOLS [J].
BOSTMEMBRUNDESRUT, M ;
DAUPHIN, G ;
KERGOMARD, A ;
RENARD, MF ;
VESCHAMBRE, H .
TETRAHEDRON, 1985, 41 (18) :3679-3682
[7]  
Buisson D., 1992, Biocatalysis, V5, P249, DOI 10.3109/10242429209014871
[8]  
Buisson D., 1990, BIOCATALYSIS, V3, P85
[9]   AN EFFICIENT SYNTHESIS OF (R)-(+)-PROPRANOLOL AND (S)-(-)-PROPRANOLOL FROM RESOLVED 5-IODOMETHYLOXAZOLIDIN-2-ONES [J].
CARDILLO, G ;
ORENA, M ;
SANDRI, S ;
TOMASINI, C .
TETRAHEDRON, 1987, 43 (11) :2505-2512
[10]   STEREOCHEMICAL CONTROL OF YEAST REDUCTIONS .2. QUANTITATIVE TREATMENT OF THE KINETICS OF COMPETING ENZYME-SYSTEMS FOR A SINGLE SUBSTRATE [J].
CHEN, CS ;
ZHOU, BN ;
GIRDAUKAS, G ;
SHIEH, WR ;
VANMIDDLESWORTH, F ;
GOPALAN, AS ;
SIH, CJ .
BIOORGANIC CHEMISTRY, 1984, 12 (02) :98-117