Unexpected participation of an unconjugated olefin during Nazarov cyclization of bridged bicyclic dienones

被引：24

作者：

Giese, S

Mazzola, RD

Amann, CM

Arif, AM

West, FG ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Gunning Lemieux Chem Ctr W5 67, Edmonton, AB T6G 2G2, Canada

[2] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 40期

关键词：

alkenes; carbocations; cyclization; cyclopropanes; diastereoselectivity;

D O I：

10.1002/anie.200501737

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Surprising rearrangements in a rigid system: A cyclopropyl ring is formed unexpectedly when a trienone substrate is subjected to the Nazarov cyclization (see scheme). The participation of the unconjugated alkene unit present in the substrate might be a consequence of the complete torquoselectivity of the initial electrocyclic closure. A subsequent rearrangement by a homo-1,5-hydrogen shift occurs cleanly to give the final product. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6546 / 6549

页数：4

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