Enzymatic kinetic resolution studies of racemic 4-hydroxycyclopent-2-en-1-one using Lipozyme IM®

被引：26

作者：

Ghorpade, SR

Bastawade, KB

Gokhale, DV

Shinde, PD

Mahajan, VA

Kalkote, UR ^{[1
]}

Ravindranathan, T

机构：

[1] Natl Chem Lab, Div Organ Chem Technol, Poona 411008, Maharashtra, India

[2] Natl Chem Lab, Div Biochem Sci, NCIM, Poona 411008, Maharashtra, India

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(99)00445-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enzymatic kinetic resolution studies of (+/-)-4-hydroxycyclopent-2-en-1-one 2 were taken up in organic solvents by transesterification with vinyl acetate and alcoholysis of its acetate 3 as an alternative to the desymmetrization of meso-cyclopentenediol to provide faster and economic access to enantiomerically pure 4-(R)tert-butyldimethylsilyloxycyclopent-2-en-1-one 1. Parameters were screened using Lipozyme IM(R) as catalyst. Although enantioselectivity observed was moderate (E=24, by alcoholysis of 3 with 2-butanol), trends in the effect of solvent, water content and alcohol structure showed useful directions for screening of other enzymes for optimization of the method to useful levels of efficiency. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4115 / 4122

页数：8

共 36 条

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