Kinetic resolution of (±)-trans- and (±)-cis-2-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters:: the key role of the leaving group

被引：37

作者：

González-Sábin, J ^{[1
]}

Gotor, V ^{[1
]}

Rebolledo, F ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 03期

关键词：

D O I：

10.1016/j.tetasy.2003.11.013

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Kinetic resolution of (+/-)-trans- and (+/-)-cis-2-phenylcyclopentanamine is effectively performed by lipase B from Candida antarctica, (CALB)-catalyzed aminolysis reaction. Whereas reaction between (+/-)-trans-2-phenylcyclopentanamine and ethyl acetate proceeds with a very high E value (>200) and conversion (50%), the corresponding acetylation of ()-cis-2-phenylcyclopentanamine happens with low E value (16) and conversion (28%). Nevertheless, this problem is overcome using other acyl donors such as (+/-)-1-phenylethyl and (+/-)-cis-2-phenylcyclopentyl methoxyacetates. The influence of the acyl donor on the CALB-catalyzed aminolysis of (+/-)-cis-2-phenylcyclopentanamine is also studied. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：481 / 488

页数：8

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