Chiral racemic α-diimines, tested in aziridination reactions with NsONHCO2Et, for the first time led to the synthesis of d,l-bidiaziridines, stereoselectively derived from the corresponding meso (E-s-trans-E)-α-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
Chiral bidiaziridines by a two-step domino aziridination of meso-α-diimines / Emanuele, Aresu; Laura, Carroccia; Fioravanti, Stefania; Gasbarri, Simona; Pellacani, Lucio; Sciubba, Fabio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 69:45(2013), pp. 9507-9511. [10.1016/j.tet.2013.08.017]
Chiral bidiaziridines by a two-step domino aziridination of meso-α-diimines
FIORAVANTI, Stefania;GASBARRI, SIMONA;PELLACANI, Lucio;SCIUBBA, FABIO
2013
Abstract
Chiral racemic α-diimines, tested in aziridination reactions with NsONHCO2Et, for the first time led to the synthesis of d,l-bidiaziridines, stereoselectively derived from the corresponding meso (E-s-trans-E)-α-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 bidiaziridinesI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
