Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers

被引：61

作者：

Qi, Xiangbing ^{[1
]}

Ready, Joseph M. ^{[1
]}

机构：

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 37期

关键词：

cycloaddition; cyclopentenones; cyclopropanes; ynols;

D O I：

10.1002/anie.200801957

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Exploiting an opening: Lewis acid promoted ring-opening of donor-acceptor cyclopropanes generates a 1,3-zwitterion; cycloaddition with a silyl ynol ether leads to a general synthesis of cyclopentenones (see scheme). Substitution is tolerated on the ynol and on all positions of the cyclopropane to give tri-, tetra-, and penta-substituted cyclopentenones in high yield. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7068 / 7070

页数：3

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