Abstract
Chiral racemic alpha-diimines, tested in aziridination reactions with NsONHCO(2)Et, for the first time led to the synthesis of (+/-)-bidiaziridines, stereoselectively derived from the corresponding meso (E-s-trans-E)-alpha-diimines. Moreover, a minor bidiaziridine isomer, probably a meso form that was lost under classical work-up conditions, can be obtained by adding water to the crude mixtures at the end of amination reactions. The results definitively prove that the imine aziridination by carbamates is a two-step domino process. The structures of the compounds were determined using 2D NMR on purified bidiaziridines. (C) 2013 Published by Elsevier Ltd.