1. Chiral bidiaziridines by a two-step domino aziridination of meso-α-diimines.
- Author
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Aresu, Emanuele, Carroccia, Laura, Fioravanti, Stefania, Gasbarri, Simona, Pellacani, Lucio, and Sciubba, Fabio
- Subjects
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CHIRALITY , *DIAZIRINES , *AZIRIDINATION , *IMINES , *CHEMICAL reactions , *STEREOSELECTIVE reactions , *CHEMICAL synthesis - Abstract
Abstract: Chiral racemic α-diimines, tested in aziridination reactions with NsONHCO2Et, for the first time led to the synthesis of (±)-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. [Copyright &y& Elsevier]
- Published
- 2013
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