α-alkylation of ketones by addition of zinc enamides to unactivated olefins

被引：38

作者：

Nakamura, M ^{[1
]}

Hatakeyama, T ^{[1
]}

Nakamura, E ^{[1
]}

机构：

[1] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 38期

关键词：

D O I：

10.1021/ja0465193

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A zinc enamide generated from the corresponding N-aryl imine undergoes addition to an unactivated olefin, such as ethylene, 1-octene, and isobutylene, to generate an alpha-alkylated gamma-zincioimine intermediate in good to excellent yield. Terminal and gem-disubstituted olefins react with >99% regioselectivity, allowing the C-C bond formation to take place at the more hindered carbon of the double bond. The organozinc intermediate undergoes further C-C bond formation with a carbon electrophile to give, upon hydrolysis of the imine, an a-alkylated ketone bearing a variety of functionalized primary, secondary, and tertiary alkyl groups.

引用

页码：11820 / 11825

页数：6

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