Application of 2,3-aziridino-γ-lactone methodology toward the enantiospecific synthesis of the (3S,4S)-isomer of dihydroxy-L-glutamic acid

Article abstract of DOI:10.1016/S0040-4020(99)00405-6

The formal synthesis of benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3- dideoxy-γ-butyrolactone (21) from D-ribose is described. Reaction of 21 with excess benzyl alcohol in the presence of boron trifluoride etherate and hydrogenolysis of the product gave