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Citation: YE Ling-Ya, WU Hong-Li, ZHANG Xiao-Long, ZHOU Jia-Dong, CAO Fei, WEI Ping. Asymmetric Synthesis of γ-Unsaturated Amino Acids Using Chiral Auxiliary[J]. Chinese Journal of Applied Chemistry, ;2009, 26(3): 346-348. shu

Asymmetric Synthesis of γ-Unsaturated Amino Acids Using Chiral Auxiliary

1.
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009

Corresponding author: CAO Fei,
Received Date: 6 February 2008
Available Online: 5 May 2008
Fund Project: 国家“九七三”重点基础研究发展计划资助项目(2003CB7160004) (2003CB7160004)

Two enantionmetric unsaturated amino acids were asymmetrically synthesized with Gly-Ni-2[N-(N'-benzylprolyl)amino]benzophenone and Ala-Ni-2[N-(N'-benzylprolyl)amino]benzophenone as chiral auxiliary to undergo replacement reaction with 3-bromopropene.The yields of two intermediates were 90%~93% and the yields of the amino acids were 75% and 80% respectively.The recovery of the Chiral auxiliary 2-[N-(N'-benzylprolyl)]-aminobenzophenone was over 90% without any loss of optical purity.All the products were characterized by NMR,MS,and optical rotation.
- amino-pentenoic acid,
- amino-methyl-pentenoic acid,
- chiral auxiliary
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