Enantioselective synthesis of α-substituted ketones by asymmetric addition of chiral zinc enamides to 1-alkenes

被引：45

作者：

Nakamura, M ^{[1
]}

Hatakeyama, T ^{[1
]}

Hara, K ^{[1
]}

Nakamura, E ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 21期

关键词：

D O I：

10.1021/ja035091p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A zinc enamide of a chiral imine derived from a ketone and (S)-valinol or (S)-t-leucinol undergoes addition to 1-alkene to generate a γ-zincioimine intermediate, which reacts with a carbon electrophile to give upon hydrolysis an optically active α-substituted ketone in good yield. The stereoselectivity of the addition reaction may reach 99% for the reaction of a cyclohexanone imine with ethylene. Copyright © 2003 American Chemical Society.

引用

页码：6362 / 6363

页数：2

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