Stereoselective synthesis of D-galactal-derived N-ethoxycarbonyl aziridine, as a new, improved synthetic protocol to glycal-derived N-activated vinyl aziridines

A new protocol for the synthesis of D-galactal-derived N-ethoxycarbonyl vinyl aziridine 1β-CO2Et, starting from tri-O-acetyl-D-glucal, is described. The new protocol constitutes a simple and fast access, with a satisfactory overall yield (5 steps, 36%), to a D-galactal-derived vinyl aziridine with a clear improvement compared with the previously described procedure leading to the structurally related N-nosyl aziridine 1β-Ns which, starting from the same precursor, proceeded through 13 steps with a low, decidedly unsatisfactory, overall yield (3%).