Electrochemical Synthesis and Reactivity of α-Alkoxy α-Amino Acid Derivatives

作者：Tameo Iwasaki, Hiroshi Horikawa, Kazuo Matsumoto, Muneji Miyoshi · 发表于：Bulletin of the Chemical Society of Japan · 年份：1979 · DOI：10.1246/bcsj.52.826 · 被引用次数：35 · 研究领域：Electrochemical Analysis and Applications

Abstract α-Alkoxy α-amino acid derivatives were synthesized in good yields by anodic oxidation of acylaminomalonic acid monoesters in alcohols. Transformation of ethyl N-acetyl-α-methoxyalaninate into ethyl N-acetyl-α,βdehydroalaninate was achieved in an excellent yield by thermal treatment of the former amino acid with a catalytic amount of ammonium bromide. Substitution of the α-alkoxy group of the α-alkoxy amino acids with nucleophiles was effected by tin tetrachloride to afford the α-substituted α-amino acids.