Trapping of Oxonium Ylides with Michael Acceptors: Highly Diastereoselective Three-Component Reactions of Diazo Compounds with Alcohols and Benzylidene Meldrum's Acids/4-Oxo-enoates

被引：4
作者：
Han, Xingchun
Gan, Minghua
Qiu, Huang
Ji, Jingjing
Zhang, Xia
Jiang, Liqing [1 ]
Hu, Wenhao
机构：
[1] E China Normal Univ, Inst Drug Discovery & Dev, Shanghai 200062, Peoples R China
来源：
SYNLETT | 2011年 / 12期
基金：
美国国家科学基金会;
关键词：
oxonium ylide; multicomponent reaction; benzylidene Meldrum's acid; 4-oxo-enoates; 1,4-addition; MULTICOMPONENT REACTIONS; ARYL DIAZOACETATES; COOPERATIVE CATALYSIS; CASCADE REACTIONS; ALDEHYDES; ACID; EFFICIENT; IMINES; STEREOCENTERS; DERIVATIVES;
D O I：
10.1055/s-0030-1260824
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Trapping of oxonium ylides with a number of Michael acceptors via a 1,4-addition fashion has been investigated. Benzylidene Meldrum's acids and 4-oxo-enoates have been found to be matched components as suitable Michael acceptors for the transformation. Thus, Rh-2(OAc)(4)-catalyzed three-component reactions of diazo compounds, alcohols, and benzylidene Meldrum's acids/4-oxo-enoates gave corresponding alpha-hydroxyesters in good yield with high to excellent diastereoselectivity. Synthetic utility of this efficient method was demonstrated by conversion of the addition product to a gamma-butyrolactone through simple procedures.
引用
收藏
页码：1717 / 1722
页数：6
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