Synthesis of chiral amino acid - derived nitrones and 1,3-dipolar cycloadditions with acrylic acid methyl ester

Abstract

The chiral nitrones derived from α-amino acids react with acrylic acid methyl ester to afford the corresponding diastereomeric isoxazolidines 9a-d. The major products are in the C-3/C-4 erythro- and C-3/C-3a trans-configuration. The nitrones 3-8 were prepared from the corresponding α-amino aldehydes, starting from L-phenylalanine and L-valine.