Dynamic kinetic resolution in the microbial reduction of alpha-monosubstituted beta-oxoesters: The reduction of 2-carbethoxy-cycloheptanone and 2-carbethoxy-cyclooctanone

被引:23
作者
Danchet, S [1 ]
Bigot, C [1 ]
Buisson, D [1 ]
Azerad, R [1 ]
机构
[1] UNIV PARIS 05,CHIM & BIOCHIM PHARMACOL & TOXICOL LAB,CNRS,URA 400,F-75270 PARIS 06,FRANCE
关键词
D O I
10.1016/S0957-4166(97)00171-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The microbial reduction of the title compounds by various yeasts or filamentous fungi strains affords the corresponding (1S,2R)- and/or (1S,2S)-hydroxyesters in good yield and ee. The determination of their absolute configuration was achieved by transformation into known 2-methylcycloalkanone stereoisomers. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1735 / 1739
页数:5
相关论文
共 37 条
[1]   Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones [J].
Abalain, C ;
Buisson, D ;
Azerad, R .
TETRAHEDRON-ASYMMETRY, 1996, 7 (10) :2983-2996
[2]   A CHEMOENZYMATIC SYNTHESIS OF (+)-CASTANOSPERMINE [J].
BHIDE, R ;
MORTEZAEI, R ;
SCILIMATI, A ;
SIH, CJ .
TETRAHEDRON LETTERS, 1990, 31 (34) :4827-4830
[3]   DIFFERENT ENZYMATIC-REACTIONS OF AN ENANTIOMERIC PAIR - SIMULTANEOUS DUAL KINETIC RESOLUTION OF A KETO ESTER BY BAKERS-YEAST [J].
BROOKS, DW ;
WILSON, M ;
WEBB, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2244-2248
[4]   A chemoenzymatic preparation of both enantiomers of omega-hydroxymethyl-substitute lactones [J].
Buisson, D ;
Azerad, R .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :9-12
[5]   MICROBIAL REDUCTION OF 1-TETRALONE 2-CARBOXYESTERS AS A SOURCE OF NEW ASYMMETRIC SYNTHONS [J].
BUISSON, D ;
CECCHI, R ;
LAFFITTE, JA ;
GUZZI, U ;
AZERAD, R .
TETRAHEDRON LETTERS, 1994, 35 (19) :3091-3094
[6]   DIASTEREOSELECTIVE AND ENANTIOSELECTIVE MICROBIAL REDUCTION OF CYCLIC ALPHA-ALKYL BETA-KETOESTERS [J].
BUISSON, D ;
AZERAD, R .
TETRAHEDRON LETTERS, 1986, 27 (23) :2631-2634
[7]   BAKERS-YEAST REDUCTIONS OF BETA-OXOPYRROLIDINECARBOXYLATES - SYNTHESIS OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-GEISSMAN-WAISS LACTONE, A USEFUL PRECURSOR TO PYRROLIZIDINE ALKALOIDS [J].
COOPER, J ;
GALLAGHER, PT ;
KNIGHT, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (12) :1313-1317
[8]   SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-METHYLENE-GAMMA-BUTYROLACTONES AND (+)-MINTLACTONE [J].
CRISP, GT ;
MEYER, AG .
TETRAHEDRON, 1995, 51 (20) :5831-5846
[9]   BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].
CSUK, R ;
GLANZER, BI .
CHEMICAL REVIEWS, 1991, 91 (01) :49-97
[10]  
DOEL BS, 1976, AUST J CHEM, V29, P2459