Biocatalytic transformation of racemates into chiral building blocks in 100% chemical yield and 100% enantiomeric excess

被引:180
作者
Strauss, UT [1 ]
Felfer, U [1 ]
Faber, K [1 ]
机构
[1] Graz Univ, Inst Organ Chem, A-8010 Graz, Austria
基金
奥地利科学基金会;
关键词
D O I
10.1016/S0957-4166(98)00490-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Biocatalytic techniques, which lead to the highly efficient transformation of a racemate into a single stereoisomeric product in (theoretically) 100% chemical yield and 100% enantiomeric excess are reviewed and their specific merits and limitations are discussed. The processes known so far can be classified into the following categories: (i) A range of methods are based on the improvement of classic kinetic resolution processes, for instance reracemization followed by repeated resolution, dynamic resolution and follow-up reactions, such as stereoinversion reactions. (ii) On the contrary, more elegant solutions are derived by employing enantioconvergent processes, which are based on the transformation of each enantiomer through stereochemically different pathways, which can be achieved by using combined chemo- and/or biocatalysis. (iii) Finally, a novel type of process for the deracemization of compounds possessing a sec-alcohol and -amino group makes use of a cyclic oxidation-reduction sequence, which is combined in a cyclic mode. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:107 / 117
页数:11
相关论文
共 55 条
[1]  
ADAMS E, 1976, ADV ENZYMOL RAMB, V44, P69
[2]  
[Anonymous], CHIRALITY IND
[3]  
AZERAD R, 1992, NATO ADV SCI I C-MAT, V381, P421
[4]   PREPARATION OF CHIRAL COMPOUNDS WITH HIGH OPTICAL PURITY BY IRRADIATION WITH CIRCULARLY POLARIZED-LIGHT, A MODEL REACTION FOR PREBIOTIC GENERATION OF OPTICAL-ACTIVITY [J].
BALAVOIN.G ;
MORADPOU.A ;
KAGAN, HB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (16) :5152-5158
[5]  
Buisson D., 1992, Biocatalysis, V5, P249, DOI 10.3109/10242429209014871
[6]  
Carnell A J, 1999, Adv Biochem Eng Biotechnol, V63, P57
[7]   PREPARATION OF OPTICALLY-ACTIVE CYCLOHEXANEDIOLS AND (+)-ALPHA-HYDROXYCYCLOHEPTANONE BY AN ENZYME-CATALYZED STEREOINVERSION/OXIDATION PROCESS [J].
CARNELL, AJ ;
IACAZIO, G ;
ROBERTS, SM ;
WILLETTS, AJ .
TETRAHEDRON LETTERS, 1994, 35 (02) :331-334
[8]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[9]  
COLLINS AN, 1992, CHIRALITY IND, V1
[10]  
COLLINS AN, 1997, CHIRALITY IND, V2