Donor-acceptor cyclopropanes as three-carbon components in a [4+3] cycloaddition reaction with 1,3-diphenylisobenzofuran

被引：134
|
作者：
Ivanova, Olga A. [1 ]
Budynina, Ekaterina M. [1 ]
Grishin, Yuri K. [1 ]
Trushkov, Igor V. [1 ]
Verteletskii, Pavel V. [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 06期
关键词：
cycloaddition; cyclopropanes; dienes; Lewis acids; synthetic methods;
D O I：
10.1002/anie.200704438
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Dienophiles with a difference: 2-Aryl 1,1-bis(alkoxycarbonyl) cyclopropanes undergo the title reaction under the catalysis of ytterbium triflate (Yb(OTf)3) in excellent yield (see scheme). Under mild reaction conditions, the major product is the less stable exo isomer. At higher temperatures, the endo isomer is obtained exclusively, as the exo cycloadduct decomposes through cycloreversion. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：1107 / 1110
页数：4
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