APPLICATION OF ERYTHRO-2-AMINO-1,2-DIPHENYLETHANOL AS A HIGHLY EFFICIENT CHIRAL AUXILIARY - HIGHLY STEREOSELECTIVE STAUDINGER-TYPE BETA-LACTAM SYNTHESIS USING A 2-CHLORO-1-METHYLPYRIDINIUM SALT AS THE DEHYDRATING AGENT

The Staudinger-type reaction of carboxylic acids with imines, using a 2-chloro-1-methylpyridinium salt as the dehydrating reagent, proceeded smoothly under mild conditions to afford the desired beta-lactams in high yields with excellent cis-selectivity. This reaction was successf ully applied to the asymmetric synthesis of beta-lactams using a chira l glycine derivative as the acid component, which was prepared from an artificial chiral auxiliary, (1S,2R)-2-amino-1,2-diphenylethanol. The corresponding beta-lactams were obtained in high yields with excellen t stereoselectivity.