Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization -: electrophilic aromatic substitution

被引：26

作者：

Browder, CC ^{[1
]}

Marmsäter, FP ^{[1
]}

West, FG ^{[1
]}

机构：

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

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2004年 / 82卷 / 02期

关键词：

domino process; electrophilic aromatic substitution; Lewis acid; Nazarov cyclization;

D O I：

10.1139/V03-203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

引用

页码：375 / 385

页数：11