从(4R)-羟基-(S)-脯氨酸合成4-取代脯氨酸(英文)  

Synthesis of 4-Substituted Prolines from (4R)-Hydroxy-(S)-Proline

作　　者：沈宗旋[1] 刘艳华[1] 陈五红[1] 石常青[1] 韩玉峰[1] 张雅文[1] 

机构地区：[1]苏州大学化学化工学院江苏省有机合成重点实验室,江苏苏州215006

出　　处：《化学研究》2005年第1期15-18,共4页Chemical Research

基　　金：supportedbytheKeyLaboratoryofOrganicSynthesisofJiangsuProvince(JSK015).

摘　　要：叙述了以(4R) 羟基 (S) 脯氨酸为原料进行的几种新型手性催化剂的简便合成方法. (4S) 苯氧基 (S) 脯氨酸 1a由N 乙氧羰基 (4R) 羟基 (S) 脯氨酸甲酯经Mitsunobu反应, C 4构型发生翻转, 水解后得到; (4R) 芳甲氧基 (S) 脯氨酸由N 叔丁氧羰基 (4R) 羟基 (S) 脯氨酸用ArCH2X醚化后脱去N 保护基得到, C 4构型不受影响.Convenient synthesis of new chiral catalysts from (4R)-hydroxy-(S)-proline is described. (4S)-phenoxy- (S)-proline was synthesized from N-ethoxycarbonyl-(4R)-hydroxy-(S)-proline methyl ester via Mitsunobu reaction with inversion of configuration at C-4, followed by hydrolysis, while (4R)-arylmethoxy-(S)-prolines were synthesized by etherification of N-boc-(4R)-hydroxy-(S)-proline using ArCH_2X followed by N-deblocking, without affecting the configuration at C-4.

关 键 词：4-取代脯氨酸 合成方法 羟脯氨酸 手性催化剂 水解反应 MITSUNOBU反应 

分 类 号：O629.7[理学—有机化学]