Efficient Synthesis of 2-Amino Acid by Homologation of β²-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile

Roba Moumne, Solange Lavielle and Philippe Karoyan*

*Synthèses, Structures et Fonctions des Molécules Bioactives, CNRS/UMR 7613, Université Pierre et Marie Curie, 4, Place Jussieu, 75252, Paris Cedex 05, France, Email: karoyanccr.jussieu.fr

R. Moumne, S. Lavielle, P. Karoyan, J. Org. Chem., 2006, 71, 3332-3334.

DOI: 10.1021/jo060316a

Abstract

A highly efficient general strategy for the synthesis of 2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction with a Mannich-type imminium electrophile is reported.

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Key Words

α-bromocarboxylic acids, diazotation, Fischer esterification, Reformatsky reaction, β-amino acids, benzylamines, Boc-protected amines

ID: J42-Y2006-1050

Efficient Synthesis of 2-Amino Acid by Homologation of β2-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile

Roba Moumne, Solange Lavielle and Philippe Karoyan*

Efficient Synthesis of 2-Amino Acid by Homologation of β²-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile