Asymmetric vinylogous Michael reaction of α,β-unsaturated ketones with γ-butenolide under multifunctional catalysis

被引：68

作者：

Huang, Huicai ^{[1
]}

Yu, Feng ^{[1
]}

Jin, Zhichao ^{[1
]}

Li, Wenjun ^{[1
]}

Wu, Wenbin ^{[1
]}

Liang, Xinmiao ^{[1
]}

Ye, Jinxing ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Minist Educ, Sch Pharm, Shanghai 200237, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 32期

基金：

中国国家自然科学基金;

关键词：

ALPHA-ACYLOXYACROLEINS; CINCHONA ALKALOIDS; ADDITION-REACTION; MANNICH-TYPE; ACID; 2-(TRIMETHYLSILYLOXY)FURANS; ALKYLATION; ALKENES;

D O I：

10.1039/c0cc01054e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and direct organocatalytic asymmetric vinylogous Michael reaction of c-butenolide with alpha,beta-unsaturated ketones was investigated with a multifunctional primary amine salt as catalyst. The reaction enables straightforward access toward synthetically versatile c-substituted butenolides from simple 2(5H)-furanone with satisfactory yields, diastereo- and enantioselectivities (up to 30 : 1 dr and 95-99% ee).

引用

页码：5957 / 5959

页数：3

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