Asymmetric synthesis of 2,3-epoxyamides by reacting monosaccharide derivatives with stabilised sulphur ylides generated in-situ: Two-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-dimethyl-carbamoylmethyl dimethyl sulphonium chloride and a 10-50% solution of sodium hydroxyde gave the corresponding 2,3-epoxyamides 5, 8 and 10, and the reaction of 1, or 5-O-trityl-2,3-O-isopropylidene-D-ribofuranose 13 with N,N-diethylcarbamoylmethyl dimethyl sulphonium chloride and a 10-50% solution of sodium hydroxyde gave the corresponding 2,3-epoxyamides 4 and 14, respectively, with high yields and variable stereoselectivity. Copyright (C) 1996 Elsevier Science Ltd