Tetrahedron

Synthesis of γ-fluoro-α-methyl-α-amino acids. A new alkylation procedure for ester imines

G Haufe, KW Laue, MU Triller, Y Takeuchi, N Shibata

Index: Haufe, Guenter; Laue, Klaus Wilhelm; Triller, Michael Ulrich; Takeuchi, Yoshio; Shibata, Norio Tetrahedron, 1998 , vol. 54, # 22 p. 5929 - 5938

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Citation Number: 18

Abstract

Deprotonation of alanine ester imines with KO'Bu in DMSO or DMF and alkylation of the formed enolates with several 2-fluoroalkyl halogenides 2 and subsequent hydrolysis of the imino and the ester groups are presented as an efficient three-step sequence for the synthesis of racemic title compounds 5.