Synthesis of Novel Sugar Derived Aziridines, As Starting Materials Giving Access to Sugar Amino Acid Derivatives

D-Erythrosyl aziridines were obtained from D-erythrosyl triazoles either by photolysis or through diazirine intermediates. These were found to undergo rich, high yielding chemistry by reaction with protic acids (HCl, BiI/HO and trifluoroacetic acid) leading to two types of furanoid sugar α-amino acids, and polyhydroxylprolines. Based on experimental evidence, reaction mechanisms have been proposed for the syntheses.