Synthesis of oxa-bridged 7- and 8-membered rings via indium-mediated annulation of 1,4- and 1,5-dicarbonyl compounds with 3-iodo-2-[(trimethysilyl)methyl]propene

被引：0

作者：

Allatabakhsh, Amir ^{[1
]}

Pham, Minh ^{[1
]}

Minehan, Thomas ^{[1
]}

机构：

[1] Calif State Univ Northridge, Dept Chem & Biochem, Northridge, CA 91330 USA

来源：

HETEROCYCLES | 2007年 / 72卷

关键词：

AQUEOUS-MEDIA; ORGANOMETALLIC REACTIONS; EFFICIENT; CONVENIENT; CATALYST; ETHERS; VINYL;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of 1,4- and 1,5-dicarbonyl compounds undergo reaction with 3-iodo-2-1(trimethylsilyl)methyllpropene in the presence of indium metal in aqueous media to produce oxa-bridged 7- and 8-membered rings in good yields. The reaction mechanism likely involves intermolecular indium allylation of one carbonyl of the substrate, followed by indium-halide promoted intramolecular allylsilane cyclization. This procedure offers an environmentally friendly alternative to the analogous tin-mediated annulation process.

引用

页码：115 / 122

页数：8