ASYMMETRIC-SYNTHESIS OF 2,3-EPOXYAMIDES BY REACTING MONOSACCHARIDE DERIVATIVES WITH STABILIZED SULFUR YLIDES GENERATED IN-SITU - 2-PHASE METHOD AND CONFIGURATIONAL ASSIGNATIONS

The reaction of 2,3-O-isopropylidene-D-glyceraldehyde 1, 24-ethylidene -D-threose 7, or 2,3:4,5-di-O-isopropylidene-D-arabinose 9 with N,N-di methyl-carbamoylmethyl dimethyl sulphonium chloride and a 10-50% solut ion of sodium hydroxyde gave the corresponding 2,3-epoxyamides 5, 8 an d 10, and the reaction of 1, or 5-O-trityl-2,3-O-isopropylidene-D-ribo furanose 13 with N,N-diethylcarbamoylmethyl dimethyl sulphonium chlori de and a 10-50% solution of sodium hydroxyde gave the corresponding 2, 3-epoxyamides 4 and 14, respectively, with high yields and variable st ereoselectivity. Copyright (C) 1996 Elsevier Science Ltd