Asymmetric Carbon-Carbon Bond Formation γ to a Carbonyl Group: Phosphine-Catalyzed Addition of Nitromethane to Allenes

被引：143

作者：

Smith, Sean W. ^{[1
]}

Fu, Gregory C. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 40期

基金：

美国国家卫生研究院;

关键词：

CONJUGATE ADDITION; UMPOLUNG ADDITION; CHIRAL PHOSPHINES; TRIPHENYLPHOSPHINE; 2,3-BUTADIENOATES; NUCLEOPHILES; HETEROCYCLES; 2-ALKYNOATES; ANNULATION; LIGANDS;

D O I：

10.1021/ja9061823

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral phosphine catalyzes the addition of a carbon nucleophile to the gamma position of an etectron-poor allene (amide-, ester-, or phosphonate-substituted), in preference to isomerization to a 1,3-diene, in good ee and yield. This strategy provides an attractive method for the catalytic asymmetric gamma functionalization of carbonyl (and related) compounds.

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收藏

页码：14231 / +

页数：4

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