Stereospecific novel glycosylation of hydroxy β-lactams via iodine-catalyzed reaction: a new method for optical resolution

Glycosylation of racemic and optically active alpha-hydroxy beta-lactams by reaction with a few glycal derivatives in the presence of catalytic amounts of iodine has provided stereospecific formation of alpha-glycosides. This method has been extended for the preparation of optically active hydroxy beta-lactams in excellent yields. The stereochemistry and nature of the glycals as well as the stereochemistry of the beta-lactam ring has a profound influence for effective glycosylation. (C) 2012 Elsevier Ltd. All rights reserved.