Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid

被引：82

作者：

Evans, DA

Barnes, DM

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 01期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(96)02259-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly enantioselective Diels-Alder reaction between acryloyl oxazolidinone and furan, catalyzed by cationic bis(4-tert-butyloxazoline)Cu(II) complex 1, is presented. Though the reaction equilibrates rapidly at -20 degrees C, reaction at -78 degrees C permits isolation of the kinetic product mixture. The synthetic utility of the reaction is demonstrated by the conversion of the cycloadduct to ent-shikimic acid. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：57 / 58

页数：2

共 18 条

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