铁催化2,3-联烯酸酯与格氏试剂的高度区域和立体选择性共轭加成反应。

Iron-catalyzed highly regio- and stereoselective conjugate addition of 2,3-allenoates with Grignard reagents.

作者信息

Lu Zhan, Chai Guobi, Ma Shengming

机构信息

Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, PR China.

出版信息

J Am Chem Soc. 2007 Nov 28;129(47):14546-7. doi: 10.1021/ja075750o. Epub 2007 Nov 7.

DOI:10.1021/ja075750o

PMID:17985902

Abstract

An efficient highly regio- and stereoselective iron-catalyzed conjugate addition of 2,3-allenoates with primary or secondary alkyl, phenyl, or vinyl Grignard reagents to synthesize multi-substituted beta,gamma-unsaturated enoates has been reported. The in situ formed magnesium dienolate may readily react with different electrophilic reagents to construct an allylic quaternary carbon at the alpha-position of the ester group.

摘要

据报道，一种高效的、具有高度区域和立体选择性的铁催化2,3-丙二烯酸酯与伯烷基、仲烷基、苯基或乙烯基格氏试剂的共轭加成反应，可用于合成多取代的β,γ-不饱和烯酸酯。原位形成的烯醇镁可容易地与不同的亲电试剂反应，在酯基的α位构建一个烯丙基季碳。