Tetrahedron

Asymmetric synthesis of α-amino acids by alkylation of N-[N-bis-(methylthio) methyleneglycyl]-2, 5-bis (methoxymethoxymethyl) pyrrolidine and enantioselective …

…, H Uchiyama, T Hayama, T Katsuki, M Yamaguchi

Index: Ikegami, Satoru; Uchiyama, Harumi; Hayama, Takashi; Katsuki, Tsutomu; Yamaguchi, Masaru Tetrahedron, 1988 , vol. 44, # 17 p. 5333 - 5342

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Citation Number: 52

Abstract

Highly diastereoselective alkylation (96% de) of α-lithiated N-[N-bis (methylthio) methyleneglycyl]-trans-2, 5-bis (methoxymethoxymethyl) pyrrolidine and subsequent hydrolysis gave various α-amino acids of high optical purity. An unusual amino acid (2S, 9S)- 2-amino-8-oxo-9, 10-epoxydecanoic acid was also synthesized enantioselectively in its N- protected form by using the alkylation of the above chiral glycine amide and asymmetric ...