Bronsted Base/Lewis Acid Cooperative Catalysis in the Enantioselective Conia-Ene Reaction

被引：156

作者：

Yang, Ting ^{[2
]}

Ferrali, Alessandro ^{[2
]}

Sladojevich, Filippo ^{[1
]}

Campbell, Leonie ^{[3
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[3] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

BIFUNCTIONAL ASYMMETRIC CATALYSIS; AMIDO COMPLEXES; ALKYNES; NUCLEOPHILE; ACTIVATION; CYANOSILYLATION; ALDEHYDES; KETONES; LIGAND;

D O I：

10.1021/ja9004859

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mutually compatible and cooperative combination of copper(I) triflate and bifunctional 9-amino-9-deoxyepicinchona-derived urea compounds for the enantioselective Conia-ene cyclization of alkyne-tethered beta-ketoester substrates is reported. The reaction is efficient, broad in scope, and easy to perform and allows access to chiral methylenecyclopentane products with high enantiocontrol. The transformation illustrates the concept of combining inactive precatatysts with inactive transition-metal-ion complexes in situ to reversibly create a catalytically active combination of the two.

引用

页码：9140 / +

页数：3

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