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

• DOI: 10.1016/j.tet.2016.12.047
• Publication Date: 2016-12-22T00:32:04Z
• Authors: Salvatore Princiotto; Valeria Di Bussolo; Vittorio Bordoni; Lucilla Favero; Stefano Crotti; Gloria Uccello Ba...; Federica Balzano; Paolo Crotti
• Keywords: 4-N-(protected)-O-glycosides; Glycals; Glycosylation; Stereoselectivity; Vinyl aziridines; 01 natural sciences; 0104 chemical sciences

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%).