The first asymmetric esterification of free carboxylic acids with racemic alcohols using benzoic anhydrides and tetramisole derivatives: an application to the kinetic resolution of secondary benzylic alcohols

被引：61

作者：

Shiina, Isamu ^{[1
]}

Nakata, Kenya ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 47期

关键词：

asymmetric esterification; kinetic resolution; free carboxylic acid; benzoic anhydride; tetramisole derivative;

D O I：

10.1016/j.tetlet.2007.09.135

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic secondary benzylic alcohols using free carboxylic acids with benzoic anhydride and tetramisole derivatives. 4-Methoxybenzoic anhydride (PMBA) is the best reagent to use in producing the corresponding esters in high ee when the reaction is catalyzed by (+)-benzotetramisole (BTM); by contrast, when non-substituted benzoic anhydride is used as a coupling reagent, the resulting optically active alcohols are obtained with high selectivities. This protocol directly produces chiral carboxylic esters from free carboxylic acids and racemic secondary alcohols by utilizing the trans-acylation process to generate mixed anhydrides from acid components and benzoic anhydride derivatives under the influence of chiral catalysts. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8314 / 8317

页数：4

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