Highly Enantioselective Pictet-Spengler Reactions with α-Ketoamide-Derived Ketimines: Access to an Unusual Class of Quaternary α-Amino Amides

被引：69

作者：

Bou-Hamdan, Farhan R. ^{[1
]}

Leighton, James L. ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 13期

基金：

美国国家科学基金会;

关键词：

asymmetric synthesis; heterocycles; ketimines; Lewis acids; Pictet-Spengler reaction; CHIRAL AUXILIARY GROUPS; SILICON LEWIS-ACID; ALLYLATION; DERIVATIVES; BENZOYLHYDRAZONES; ALDIMINES; REAGENT; ESTERS; ETHER; IONS;

D O I：

10.1002/anie.200806110

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

"Quat's" the story? N-Aryl amides are effective directing/activating groups for chlorosilane Lewis acids. This aspect has been exploited for the development of the first simple and general method for the highly enantioselective Pictet-Spengler reaction of ketimines derived from α-ketoamides leading to quaternary α-amino acid derivatives (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2403 / 2406

页数：4