利用手性相转移催化剂不对称合成旋光性2,4,6-三甲基苯丙氨酸  

Asymmetric Synthesis of Optical Activity 2,4,6-Trimethyl Phenylalanine by Chiral Phase Transfer Catalyst

作　　者：周鸿睿[1] 李靖柯[1] 彭俊[1] 冯悦[1] 胡湘南[1] 

机构地区：[1]重庆医科大学药学院,重庆市渝中区医学院路1号400016

出　　处：《光谱实验室》2012年第4期2042-2046,共5页Chinese Journal of Spectroscopy Laboratory

基　　金：重庆自然科学基金项目(CSTC;2006BB5286)

摘　　要：以甘氨酸(Ⅰ)为原料,在羧基保护下合成底物苯亚甲氨基乙酸乙酯(Ⅲ),然后经手性催化剂(一)-N-苄基氯化辛可尼定(BCDC)和(+)-N-苄基氯化辛可宁(BCNC)的催化,酸水解得到旋光性的2,4,6-三甲基苯丙氨酸(V-2,V-3),总收率分别为28%和31%,比旋光度分别为[a]_D^(20)=+16°和[α]_D^(20)=—9°。以氯化三乙基苄胺(TEBA)作非手性相转移催化剂得到了消旋2,4,6-三甲基苯丙氨酸(V-1),总收率为32%。并探讨了利用手性相转移催化剂不对称合成的反应机理。Synthesis of the substrate benzylidene amino acetate（Ⅲ） under protection of carboxyl groups with glycine（Ⅰ） as raw material,then the compound was catalyzed by the chiral catalyst, including（-）-N-benzylcinchonadinium chloride（BCDC） and（＋）-N-benzylcinchoninium chloride （BCNC）,and were carried out by acid hydrolysis to obtain the optical activity 2,4,6-trimethyl phenylalanine（V-2,V-3）,and the total yields were respectively 28%and 31%,and the specific rotations of product were respectively[α]D20=＋16°and[α]D20=-9°.The recemization 2,4,6-trimethylphenylalanine（V-1） was synthetized with chloride triethyl benzylamine（TEBA） as the achirality phase transfer catalyst,and the total yield was 32%.The reaction mechanism of asymmetric synthesis by the chiral phase transfer catalyst was investigated.

关 键 词：手性相转移催化 2 4 6-三甲基苯丙氨酸 不对称合成 

分 类 号：O657.33[理学—分析化学] O657.2[理学—化学]