Intramolecular Michael reactions of aliphatic aldehyde enolates generated by imidazolium carbenes

被引：10
|
作者：
Kim, Hyoungsu [1 ]
Byeon, Seong Rim [1 ]
Leed, Marina G. D. [1 ]
Hong, Jiyong [1 ]
机构：
[1] Duke Univ, Dept Chem, Durham, NC 27708 USA
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 19期
基金：
美国国家科学基金会;
关键词：
Intramolecular Michael reaction; N-heterocyclic carbene; Aldehyde enolate; Bronsted base; N-HETEROCYCLIC CARBENES; BASICITY; ALCOHOLS;
D O I：
10.1016/j.tetlet.2011.03.008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Due to the high reactivity of the formyl group under either basic or acidic reaction conditions required for the direct generation of aldehyde enolates, intramolecular Michael additions of aldehyde enolates to alpha,beta-unsaturated carbonyl compounds have been underexplored for the stereoselective synthesis of carbocyclic compounds. The intramolecular Michael reaction of aldehyde enolates generated by imidazolium carbenes was explored for the synthesis of cyclopentane aldehydes. The imidazolium carbenes were used as Bronsted bases to directly generate the aldehydes enolates. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2468 / 2470
页数：3
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