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
收藏
页码：7068 / 7070
页数：3
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