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Citation: REN Xing-Hua, LI Zhen-Jiang, SUN Ying-Jie, LI Wei-Si. Asymmetric Synthesis of R-and S-α-Methyl-p-methoxy-phenylalanines by 'Alanine Equivalent' Method[J]. Chinese Journal of Applied Chemistry, ;2007, 24(2): 235-237. shu

Asymmetric Synthesis of R-and S-α-Methyl-p-methoxy-phenylalanines by 'Alanine Equivalent' Method

1.
College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009

Corresponding author: LI Zhen-Jiang,
Received Date: 13 April 2006
Available Online: 18 June 2006
Fund Project: 国家高技术研究发展计划(2003AA235051)资助项目 (2003AA235051)

Optically active(R)-and(S)-α-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%,respec-tively,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.
- disubstituted amino acid,
- asymmetric,
- chiral Ni(Ⅱ) complex,
- Schiff base
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