Asymmetric Olefin Isomerization of Butenolides via Proton Transfer Catalysis by an Organic Molecule

被引：118

作者：

Wu, Yongwei ^{[1
]}

Singh, Ravi P. ^{[1
]}

Deng, Li ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 32期

关键词：

ENANTIOSELECTIVE PROTONATION; HYDROGEN-BOND; ALLYLIC ALCOHOLS; GAMMA-LACTONES; SUBSTRATE; ACIDITY; DIHYDROXYLATION; ALLYLAMINES; ENANTIOMERS; EFFICIENT;

D O I：

10.1021/ja205674x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented enantioselective and general olefin isomerization was realized via biomimetic proton transfer catalysis with a new chiral organic catalyst. A broad range of mono- and disubstituted beta,gamma-unsaturated butenolides were transformed into the corresponding chiral alpha,beta-unsaturated butenolides in high enantioselectivity and yield in the presence of as low as 0.5 mol % catalyst. Mechanistic studies have revealed the protonation as the rate-determining step.

引用

收藏

页码：12458 / 12461

页数：4

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