Polymeric chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids
Polymeric chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids
复制标题
DOI：
10.1016/j.tet.2007.05.076
复制
发表时间：
2007-08-13
期刊：
影响因子：
2.1
通讯作者：
Jeong, Byeong-Seon
中科院分区：
文献类型：
--
作者：
Lee, Jeong-Hee;Yoo, Mi-Sook;Jeong, Byeong-Seon
以金鸡纳生物碱为原料，设计了一系列二聚/三聚手性季铵盐作为高效实用的手性相转移催化剂。介绍了用于合成光学活性α-氨基酸衍生物的二聚PTC的发展和适合于二聚PTC的反应变量的优化的细节。在N-（二苯基亚甲基）甘氨酸叔丁酯（1）的催化相转移烷基化反应中，1，3-苯基和2，7-萘基连接的二聚PTC表现出优异的催化活性和对映选择性。使用二聚PTC，特别是2，7-萘基-二聚体41，以非常实用的方式获得了具有高对映体纯度的多种α-氨基酸衍生物。(C)2007爱思唯尔有限公司版权所有。
A series of dimeric/trimeric chiral quaternary ammonium salts derived from cinchona alkaloids were designed as efficient and practical chiral phase-transfer catalysts (PTCs). Presented are the details on the development of the dimeric PTCs for the synthesis of optically active alpha-amino acid derivatives and the optimization of the reaction variables suitable for the dimeric PTCs. The 1,3-phenyl- and the 2,7-naphthyl-linked dimeric PTCs showed excellent catalytic capability on the reactivity and enantioselectivity in the catalytic phase-transfer alkylation of N-(diphenylmethylene) glycine tert-butyl ester (1). A variety of alpha-amino acid derivatives were obtained with high enantiopurities using the dimeric PTCs, especially the 2,7-naphthyl-dimer 41, in a very practical manner. (C) 2007 Elsevier Ltd. All rights reserved.