Catalytic Enantioselective [2,3]-Rearrangements of Amine N-Oxides

被引：43

作者：

Bao, Hongli ^{[1
]}

Qi, Xiangbing ^{[1
]}

Tambar, Uttam K. ^{[1
]}

机构：

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 05期

关键词：

MEISENHEIMER REARRANGEMENT; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; SECONDARY ALCOHOLS; CHIRALITY TRANSFER; ALLYLIC ALCOHOLS; DERIVATIVES; ALDEHYDES; CARBONYL; SYSTEMS;

D O I：

10.1021/ja110500m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first Pd-catalyzed enantioselective [2,3]-rearrangement of allylic amine N-oxides is described, which formally represents an asymmetric Meisenheimer rearrangement. The mild reaction conditions enable the synthesis of chiral nonracemic aliphatic allylic alcohol derivatives with reactive functional groups. On the basis of preliminary studies, a cyclization-mediated mechanism is proposed.

引用

页码：1206 / 1208

页数：3

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