Synthesis of cinchonidinium salts containing sulfonamide functionalities and their catalytic activity in asymmetric alkylation reactions

被引：2
|
作者：
Itsuno, Shinichi [1 ]
Yamamoto, Shunya [1 ]
Takata, Shohei [1 ]
机构：
[1] Toyohashi Univ Technol, Dept Environm & Life Sci, Toyohashi, Aichi 4418580, Japan
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 44期
关键词：
Cinchonidinium salt; Organocatalyst; Sulfonamide; Asymmetric alkylation; PHASE-TRANSFER CATALYSTS; ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE SYNTHESIS; GLYCINE IMINE;
D O I：
10.1016/j.tetlet.2014.09.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Various kinds of 4-(bromomethyl)benzenesulfonamides were prepared as quaternization reagent of cinchonidine. Cinchonidinium salts obtained from the quaternization of cinchonidine with 4-(bromomethyl)benzenesulfonamide showed highly enantioselective catalytic activity in the asymmetric benzylation of N-(diphenylmethylene)glycine tert-butyl ester. The corresponding phenylalanine derivative was obtained in high yield with a high level of enantioselectivity, up to 98% ee. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6117 / 6120
页数：4
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