Enantioselective Organo-SOMO Cascade Cycloadditions: A Rapid Approach to Molecular Complexity from Simple Aldehydes and Olefins

被引：104

作者：

Jui, Nathan T. ^{[1
]}

Lee, Esther C. Y. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 29期

关键词：

ALPHA-ARYLATION; ACTIVATION; CATALYSIS; CHEMISTRY;

D O I：

10.1021/ja104313x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.

引用

页码：10015 / 10017

页数：3

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