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STRUCTURE OF SOLVENT AFFECTS ENANTIOSELECTIVITY OF LIPASE-CATALYZED TRANSESTERIFICATION

被引：63
作者：
NAKAMURA, K
KINOSHITA, M
OHNO, A
机构：
[1] Institute for Chemical Research, Kyoto University Uji, Kyoto
来源：
TETRAHEDRON | 1995年 / 51卷 / 32期
关键词：
D O I：
10.1016/0040-4020(95)00470-S
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lipase-catalyzed transesterification of (rac)-6-methyl-5-hepten-2-ol (sulcatol) with vinyl acetate has been studied in various solvents and the effect of solvent on the enantioselectivity has been discussed from the viewpoint of molecular shape of the solvent. Alkanes and ethers are selected as solvents. Enantioselectivity of a reaction in a structurally linear solvent is higher than that in the corresponding branched chain solvent. Furthermore, the enantioselectivity decreases specifically with the increase in the ring size of solvent molecule. Thus, lipase recognizes not only the structure of substrate but also that of solvent.
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页码：8799 / 8808
页数：10
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