Direct carbon-carbon bond formation via chemoselective soft enolization of thioesters: A remarkably simple and versatile crossed-Claisen reaction applied to the synthesis of LY294002

被引：47

作者：

Zhou, Guoqiang ^{[1
]}

Lim, Daniel ^{[1
]}

Coltart, Don M. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 17期

关键词：

D O I：

10.1021/ol801498u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thioesters undergo chemoselective soft enolization and acylation by N-acylbenzotriazoles on treatment with MgBr(2)center dot OEt(2) and i-Pr(2)NEt to give beta-keto thioesters. Prior enolate formation is not required, and the reaction is conducted using untreated CH(2)Cl(2) open to the air. The coupled products are stable synthetic equivalents of beta-keto acids and can be converted directly into beta-keto esters, beta-keto amides, and beta-diketones under mild conditions. The utility of this carbon-carbon bond-forming method is shown through the synthesis of the PI3-K inhibitor LY294002.

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收藏

页码：3809 / 3812

页数：4

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