Enantioselective organocatalytic reductive amination

被引：637

作者：

Storer, RI ^{[1
]}

Carrera, DE ^{[1
]}

Ni, Y ^{[1
]}

MacMillan, DWC ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 01期

关键词：

D O I：

10.1021/ja057222n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines and provided a highly stereoselective method for the reductive amination of heterocyclic amines. A diverse spectrum of ketone and amine substrates can be accommodated in high yield and excellent enantioselectivity. This new protocol realizes a key benefit of reductive amination versus imine reduction, in that ketimines derived from alkyl-alkyl ketones are unstable to isolation, a fundamental limitation that is comprehensively bypassed using this direct organocatalytic reductive amination. Copyright © 2006 American Chemical Society.

引用

页码：84 / 86

页数：3

共 36 条

[1] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].