Ruthenium-catalyzed hydrative cyclization of 1,5-enynes

被引：55

作者：

Chen, YY ^{[1
]}

Ho, DM ^{[1
]}

Lee, C ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 35期

关键词：

D O I：

10.1021/ja053462r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ruthenium-catalyzed hydrative cyclization of enynes has been developed. The reaction converts a range of 1,5-enynes bearing terminal alkyne and Michael acceptor moieties into cyclopentanone derivatives. From extensive catalyst screening experiments, a trinuclear ruthenium complex, [Ru3(dppm)3Cl5]PF6, has been identified to be an effective catalyst in mediating the 1,1-difunctionalization of alkynes. It is proposed that this novel umpolung reaction proceeds through the formation of a ruthenium vinylidene, anti-Markovnikov hydration, and intramolecular Michael addition of an acyl ruthenium to the alkene. Copyright © 2005 American Chemical Society.

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页码：12184 / 12185

页数：2

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