A new approach to the Nazarov reaction via sequential electrocyclic ring opening and ring closure

被引：68

作者：

Grant, Tina N. ^{[1
]}

West, F. G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 29期

关键词：

D O I：

10.1021/ja063421a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Regioselective dichlorocyclopropanation of 2-silyloxydienes furnishes vinylcyclopropanol silyl ethers in good yield. Treatment with silver(I) at room temperature effects disrotatory electrocyclic opening to a 2-chloro-3-silyloxypentadienyl cation, which then undergoes conrotatory (Nazarov) electrocyclization to provide chlorocyclopentenones. This two-step sequence offers a convenient and mild alternative to the standard Nazarov cyclization protocol via a formal 4+1 construction and furnishes products containing useful halogen functionality. In one case possessing a pendant phenyl group, interrupted Nazarov reaction to give a benzohydrindenone was observed. Copyright © 2006 American Chemical Society.

引用

页码：9348 / 9349

页数：2

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