A Simple Synthesis of α, β-Unsaturated γ-Aminobutyric Acid (GABA) Derivatives from Enamines

…, C Gussetti, HC Militzer, MS Baird, A de Meijere

Index: Henniges; Gussetti; Militzer; Baird; De Meijere Synthesis, 1994 , # 12 p. 1471 - 1475

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Citation Number: 4

Abstract

Bromination of enamines 3b—g at—78 C and subsequent treatment of the resulting iminium salts 4b-g with excess rert-butyl lithioacetate leads to tert-butyl 4-(N, N-dialkylamino) carboxylates 9b—g in good to very good yields. Ester cleavage of the dibenzylamino derivative 9d with trifluoroacetic acid yields the corresponding acid 10. Subsequent catalytic hydrogenation of 10 leads to the fully deprotected 4-amino-4-methylpentanoic acid (12) in ...