2-Carbamoylaziridine (Leakadine): diastereoselective transformations and stereoelectronic effect*

Abstract

Diastereoselective transformations of Leakadine were discovered: dimerization during melting or heating in CHCl3 with the formation of one diastereomer. The obtained dimer reacts with methyl isocyanate under mild conditions with the formation of an N-methylcarbamoyl derivative – also in the form of one diastereomer. In the diastereoselective reaction of Leakadine with dimethyl formamide dimethyl acetal, 2-dimethylamino-1,3-diazabicyclo[3.1.0]hexan-4-one was obtained. The reaction of Leakadine with perfluoroisobutylene was studied.