Asymmetric synthesis of 2,3-epoxyamides by reacting monosaccharide derivatives with stabilised sulphur ylides generated in-situ: Two-phase method and configurational assignations

Article abstract of DOI:10.1016/0957-4166(96)00249-2

The reaction of 2,3-O-isopropylidene-D-glyceraldehyde 1, 2,4-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.