Diastereoselective synthesis of 1-α-phenylethyl-3,3-dimethyldiaziridine. Conformation and configuration of three-membered ring nitrogen heterocycles containing an asymmetric substituent on the nitrogen atom

The synthesis of 1-(S)-α-phenylethyl-3,3-dimethyldiaziridine from N-(S)-α-phenylacetonimine and hydroxylamine-O-sulfonic acid has been carried out with high diastereoselectivity. The absolute configuration of the diastereomers was established by comparison with oxaaziridine analogs based on their NMR and CD spectra, and atom-atomic potential calculations. A test has been proposed to establish the absolute configuration of N-α-phenylethyl-substituted three-membered ring heterocycles using NMR, and the mechanism of epimination of imines is discussed, which is similar to their oxidation mechanism.