A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric Mannich Reactions of N-Boc-Protected Imines

被引：109

作者：

Kano, Taichi ^{[1
]}

Yamaguchi, Yukako ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 10期

基金：

日本学术振兴会;

关键词：

asymmetric catalysis; diastereoselectivity; enantioselectivity; Mannich reaction; organocatalysis; HIGHLY ENANTIOSELECTIVE ROUTE; ALPHA-AMINO; ACID-DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; GENERAL ORGANOCATALYST; UNMODIFIED ALDEHYDES; ALDOL REACTIONS; BETA-LACTAMS; ONE-POT; ALCOHOLS;

D O I：

10.1002/anie.200805628

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The moderate nucleophilicity of the axially chiral amino sulfonamide (S)-1 suppresses the problematic side reactions, including aldol reactions, in the asymmetric Mannich reaction of N-Boc-protected imines with aldehydes. The corresponding adducts are obtained in good yield and excellent stereoselectivity (see scheme; Boc=tert-butoxycarbonyl, Tf=trifluoromethanesulfonyl). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1838 / 1840

页数：3