Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Tertiary Allylic Trichloroacetimidates with Anilines

被引：96

作者：

Arnold, Jeffrey S. ^{[1
]}

Nguyen, Hien M. ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 20期

基金：

美国国家科学基金会;

关键词：

CHIRAL DIENE LIGANDS; ENANTIOSELECTIVE ALLYLATION; QUATERNARY STEREOCENTERS; AMINATION; AMINES; ALKYLATION; ARYLATION; REARRANGEMENT; 1,2-ADDITION; RESOLUTION;

D O I：

10.1021/ja302223p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rhodium-catalyzed regio- and enantioselective amination of racemic tertiary allylic trichloroacetimidates with a variety of aniline nucleophiles is a direct and efficient route to chiral alpha,alpha-disubstituted allylic N-arylamines. We describe the first dynamic kinetic asymmetric transformations of racemic tertiary allylic electrophiles with anilines utilizing a chiral diene-ligated rhodium catalyst. The method allows for the formation of alpha,alpha-disubstituted allylic N-arylamines in moderate to good yields with good to excellent levels of regic- and enantioselectivity.

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收藏

页码：8380 / 8383

页数：4

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