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

Abstract A new protocol for the synthesis of d -galactal-derived N -ethoxycarbonyl vinyl aziridine 1β-CO 2 Et , 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%).