SYNTHESIS OF SOME NEW SUGAR BASED 3, 3-DISUBSTITUTED MONOCYCLIC Β-LACTAMS BY ASYMMETRIC [2+2] CYCLOADDITION REACTIONS

Abstract

Synthesis of some new monocyclic β-lactams containing a quaternary carbon center via a [2+2]cycloaddition reaction is described. The reaction of achiral diphenyl ketene with chiral aldimines derivedfrom chiral 2, 3, 4, 6-tetra-O-acetyl-β-D-galactopyranosylamine, 2, 3, 4, 6-tetra-O-acetyl-β-Dglucopyranosylamine and different benzaldehydes resulted in the formation of β-lactams as singlediastereomers.