Enzymatic resolution of endo-bicyclo[4.1.0]heptan-2-ols

被引：3

作者：

Barnier, JP ^{[1
]}

Rayssac, V ^{[1
]}

Morisson, V ^{[1
]}

Blanco, L ^{[1
]}

机构：

[1] UNIV PARIS 11,INST CHIM MOL ORSAY,LAB CARBOCYCLES,CNRS,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(97)10299-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active endo-bicyclo[4.1.0]heptan-2-ols compounds were prepared by lipase-catalyzed transesterifications with the racemic alcohols. High enantioselectivities and reaction rates were observed using the lipase from Candida antarctica. (C) 1997 Elsevier Science Ltd.

引用

页码：8503 / 8506

页数：4

共 20 条

[1] ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].

ADER, U ;

BREITGOFF, D ;

KLEIN, P ;

LAUMEN, KE ;

SCHNEIDER, MP .

TETRAHEDRON LETTERS, 1989, 30 (14) :1793-1796

[2] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (-)-ROTHROCKENE, A NON-HEAD-TO-TAIL MONOTERPENE [J].

BARBACHYN, MR ;

JOHNSON, CR ;

GLICK, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2746-2748

[3] Some novel electron transfer mediated cascade ring-opening reactions of bicyclo[4.1.0]ketones [J].

Batey, RA ;

Harling, JD ;

Motherwell, WB .

TETRAHEDRON, 1996, 52 (35) :11421-11444

[4] 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

[5] 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

[6] 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

[7] Enantiomerically pure cyclopropanoid nucleoside analogues: Synthesis and analysis [J].

Csuk, R ;

vonScholz, Y .

TETRAHEDRON, 1996, 52 (18) :6383-6396

[8] PREPARATION OF CYCLIC CYCLOPROPYLCARBINOLS [J].

DAUBEN, WG ;

BEREZIN, GH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (04) :468-&

[9] A COMPARISON OF (CHLOROMETHYL)ZINC AND (IODOMETHYL)ZINC CYCLOPROPANATION REAGENTS [J].

DENMARK, SE ;

EDWARDS, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :6974-6981

[10] ENZYMATIC-HYDROLYSIS OF CYCLOPROPANES - TOTAL SYNTHESIS OF OPTICALLY PURE DICTYOPTERENE-A AND DICTYOPTERENE-C' [J].

GRANDJEAN, D ;

PALE, P ;

CHUCHE, J .

TETRAHEDRON, 1991, 47 (07) :1215-1230

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