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

页码：6117 / 6120

页数：4

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