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.

Authors: R. G. Kostyanovsky, G. K. Kadorkina, O. N. Krutius, and I. I. Chervin.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (6), pp 869-874

http://link.springer.com/article/10.1007/s10593-012-1068-1