摘要
以R-及S-2-[N-(N′-苄基)脯氨酰-氨基]-二苯甲酮的丙氨酸席夫碱Ni(Ⅱ)配合物和p-甲氧基苄基氯反应制备R-及S-α-甲基-(p-甲氧基)苯丙氨酸。探讨了碱对反应立体选择性的影响,确定了最佳反应条件: R-或S-2-[N-(N′-苄基)脯氨酰-氨基]-二苯甲酮的丙氨酸席夫碱Ni(Ⅱ)配合物与p-甲氧基苄基氯的摩尔比为1:1．1,反应时间2 h。R-及S-α-甲基-(p-甲氧基)苯丙氨酸的总收率分别为71．3％和70．9％,e．e．达97．5％,手性辅基2-[N-(N′-苄基)脯氨酰-氨基]．二苯甲酮的回收率为90％～95％。同时用核磁共振和旋光测试技术对产物进行了表征。
Optically active （R）- and （S）-ot-methyl-p-methoxy-phenylalanine were synthesized by electro- philic alkylation of Ni（ Ⅱ ） complexes of alanine Schiff base with p-methoxybenzyl chloride. The effect of base on the stereoselectivity of the reaction was investigated. The optimal reaction conditions were that the molar ratio of Ni （ Ⅱ ） complexes of alanine Schiff base to p-methoxybeznyl chloride was 1 ： 1.1, and reaction time was 2 h. The yields of （R）- and （S）-α-methyl-p-methoxy-phenylalanines were 71.3% and 70. 9%, respectively, and the e. e. was up to 97.5%. Chiral auxiliary 2-[ N-（N＇-benzylprolyl） ]-aminobenzophenone was recovered in a 90% to 95% yield without any loss of the optical purity. The products were characterized by NMR and optical rotation
出处
《应用化学》
CAS
CSCD
北大核心
2007年第2期235-237,共3页
Chinese Journal of Applied Chemistry
基金
国家高技术研究发展计划(2003AA235051)资助项目
