Chemo-enzymatic preparation of optically active endo-bicyclo[4.1.0]heptan-2-ols

被引:15
作者
Barnier, JP [1 ]
Morisson, V [1 ]
Volle, I [1 ]
Blanco, L [1 ]
机构
[1] Univ Paris Sud, Inst Chim Mol Orsay, Lab Carbocycles, CNRS, F-91405 Orsay, France
关键词
D O I
10.1016/S0957-4166(99)00099-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Resolutions of endo-bicyclo[4.1.0]heptan-2-ols were achieved by acylation in the presence of lipase from Candida antarctica (Novozym(R)). The (1S,2R,6R) enantiomers reacted faster and the enantiomeric ratios were between 60 and 800 for the 6-substituted bicycloalkanols. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1107 / 1117
页数:11
相关论文
共 80 条
[11]   SPECIFIC BETA-SCISSION OF 3BETA,5-CYCLOCHOLESTAN-6-YL RADICAL [J].
BECKWITH, ALJ ;
PHILLIPOU, G .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (01) :123-131
[12]  
BISHOF EW, 1992, J PHOTOCH PHOTOBIO A, V63, P249
[13]   Synthesis of enantiomericaliy pure cis- and trans-1,2-diaminoindanes [J].
Bit, C ;
Mitrochkine, AA ;
Gil, G ;
Pierrot, M ;
Réglier, M .
TETRAHEDRON-ASYMMETRY, 1998, 9 (18) :3263-3273
[14]   LIPASE-MEDIATED RESOLUTION OF 2-CYCLOHEXEN-1-OLS AS CHIRAL BUILDING-BLOCKS EN-ROUTE TO EBURNANE ALKALOIDS [J].
CARREA, G ;
DANIELI, B ;
PALMISANO, G ;
RIVA, S ;
SANTAGOSTINO, M .
TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :775-784
[15]   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
[16]  
CHEN Y, 1992, LINCHAN HUAXUE YU GO, V12, P159
[17]  
CHEN YZ, 1987, CHROMATOGRAPHIA, V23, P502
[18]   SEQUENTIAL RADICAL RING-CLOSURE RADICAL RING-OPENING - USE IN THE PREPARATION OF BENZOFURANS [J].
CLIVE, DLJ ;
DAIGNEAULT, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5285-5289
[19]   USE OF RADICAL RING-OPENING FOR INTRODUCTION OF ALKYL AND SUBSTITUTED ALKYL-GROUPS WITH STEREOCHEMICAL CONTROL - A SYNTHETIC APPLICATION OF CYCLOPROPYLCARBINYL RADICALS [J].
CLIVE, DLJ ;
DAIGNEAULT, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3801-3814
[20]   SYNTHESIS OF ALTERNATING HYDROXY-SUBSTITUTED AND METHYL-SUBSTITUTED HYDROCARBONS BY OXYMERCURATION OF CYCLOPROPYLCARBINOLS [J].
COLLUM, DB ;
STILL, WC ;
MOHAMADI, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2094-2096