Stereoselective Nazarov cyclizations of bridged bicyclic dienones

被引：27

作者：

Mazzola, RD ^{[1
]}

White, TD ^{[1
]}

Vollmer-Snarr, HR ^{[1
]}

West, FG ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol051169q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bridged bicyclic dienones underwent silyl-directed Nazarov cyclization with generally very high diastereoselectivity. In most cases, a strong preference for cyclization to the product with an exo-disposed cyclopentenone was seen. However, the presence of additional unsaturation in the three-carbon bridge of a bicyclo[3.2.1]octadiene system caused complete reversal in selectivity with exclusive formation of the endocyclopentenone. The observed selectivities are believed to result from a combination of steric and electronic effects.

引用

页码：2799 / 2801

页数：3

共 34 条

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