Asymmetric syntheses of .BETA.-amino acid and aspartic acid by Reformatsky reaction.

Abstract

Asymmetric syntheses of β-amino acids and aspartic acid were achieved by the reaction of optically active Schiff bases prepared from aldehydes and optically active amines, R (+)- and S (-)-α-methylbenzylamines, with Reformatsky reagents in the range of 18-28% optical purities. When the Schiff bases having R (+)-amino component were used in the reaction, (S)-β-amino acids and (R)-aspartic acid were formed. The use of the Schiff bases involving S (-)-amino component gave (R)-β-amino acids and (S)-aspartic acid. The reaction of Schiff bases prepared from aldehydes and benzylamine with optically active Reformatsky reagents having l-menthyl ester gave (S)-β-amino acids and (R)-aspartic acid in the range of 2-5% optical purities. The steric course were also presumed.