Mechanistic Rationalization of Organocatalyzed Conjugate Addition of Linear Aldehydes to Nitro-olefins

被引：121

作者：

Bures, Jordi ^{[1
]}

Armstrong, Alan ^{[2
]}

Blackmond, Donna G. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 23期

基金：

英国工程与自然科学研究理事会;

关键词：

ASYMMETRIC MICHAEL-ADDITIONS; BOND-FORMING REACTIONS; ENAMINE CATALYSIS; C-N; NITROOLEFINS; NITROALKENES; CYCLOHEXANONE; CHEMISTRY; BEHAVIOR; ETHERS;

D O I：

10.1021/ja203660r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

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收藏

页码：8822 / 8825

页数：4

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