Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of α-alkyl- and α,α-dialkyl-α-amino acids:: application to the short asymmetric synthesis of BIRT-377
Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of α-alkyl- and α,α-dialkyl-α-amino acids:: application to the short asymmetric synthesis of BIRT-377
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DOI：
10.1016/j.tetlet.2005.09.185
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发表时间：
2005-12-05
影响因子：
1.8
通讯作者：
Maruoka, K
中科院分区：
文献类型：
--
作者：
Han, ZF;Yamaguchi, Y;Maruoka, K
从已知的、容易获得的（S）-4，5，6，4 ′，5 ′，6 ′-六甲氧基联苯二甲酸方便地制备了高活性相转移催化剂。该催化剂表现出较高的催化性能（0.01-1摩尔%）在N-的不对称烷基化反应中（二苯基亚甲基）甘氨酸叔丁酯和N-（对氯苯亚甲基）丙氨酸叔丁酯与现有的手性相转移催化剂相比，从而实现了用于高度实用的对映选择性合成结构多样的天然和非天然α-烷基-α-氨基酸以及α，α-二烷基-α-氨基酸。(c)2005爱思唯尔有限公司保留所有权利。
A highly active phase-transfer catalyst was conveniently prepared from the known, easily available (S)-4,5,6,4',5',6'-hexamethoxybiphenyldicarboxylic acid. This catalyst exhibited the high catalytic performance (0.01-1 mol %) in the asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester and N-(p-chlorophenylmethylene)alainne tert-butyl ester compared to the existing chiral phase-transfer catalysts, thereby allowing to realize a general and useful procedure for highly practical enantioselective synthesis of structurally diverse natural and unnatural alpha-alkyl-alpha-amino acids as well as alpha,alpha-dialkyl-alpha-amino acids. (c) 2005 Elsevier Ltd. All rights reserved.