Stereoselective Synthesis of β³-Amino Acids and β-Oligopeptides Promoted by Organoselenium Intermediates

Abstract

Propargylic amines can be valid precursors for the synthesis of β³-amino acids. This can be effected by a selenium-mediated conversion of the carbon–carbon triple bond to a, Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols, or the amine of an amino acid derivative to give β³-amino acids, β³-amino esters, or mixed peptides, respectively.

Keywords:

• α-Amino acids
• β-amino acids
• propargylic amines
• selenium

Acknowledgments

Financial support from MIUR, National Projects PRIN 2007, Consorzio CINMPIS, Bari, and University of Perugia is gratefully acknowledged.