One step access to oxindole-based ß-lactams through Ugi four-center three-component reaction.

ABSTRACT

A multicomponent Ugi reaction involving isatin, isocyanide and ß-amino acid components has been developed. The reactions proceeded smoothly to give ß-lactam-containing 3,3-disubstituted oxindoles in only one step and generally high yields. When chiral, non racemic, ß-amino acids were used, products were obtained as enantiomerically pure ß-lactams diastereoisomers, whose relative stereochemistry was determined by X-ray analysis. For one compound, a weak antibacterial activity has been preliminarily highlighted.