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

被引：83
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：
美国国家科学基金会; 美国国家卫生研究院;
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
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页码：57 / 58
页数：2
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