Tetrahedron letters

Enantioselective synthesis of (S)-2-(Aminomethyl) butanedioic acid using chiral β-alanine α-enolate equivalents

E Arvanitis, M Motevalli, PB Wyatt

Index: Arvanitis, Elena; Motevalli, Majid; Wyatt, Peter B. Tetrahedron Letters, 1996 , vol. 37, # 24 p. 4277 - 4280

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Citation Number: 28

Abstract

(S)-2-(Aminomethyl) butanedioic acid (6) can been synthesised by stereoselective alkylation of the Na enolates of acyloxazolidinones 1a and 1b with methyl bromoacetate, then oxidation of the vinyl or dimethoxyphenyl substituent to a carboxyl group, followed by Curtius rearrangement and deprotection. The absolute configuration of 6 has been correlated with that of (S)-1-phenylethylamine by a combination of crystallographic and chemical means.