Room temperature ring-opening cyclization reactions of 2-vinylaziridines with isocyanates, carbodiimides, and isothiocyanates catalyzed by
2-Vinylaziridines undergo cycloaddition reactions with various heterocumulenes, in the presence of [Pd(OAc)(2)] and PPh(3), at room temperature and 1 atm pressure, regioselectively affording five-membered ring products in moderate to high yields. The mixture of stereoisomers obtained by reactions employing cis-1-butyl-2-vinyl-3-methylaziridine as the reactant provides evidence for a mechanism involving a eta(3)-eta(1)-eta(3) interconversion of a (pi-allyl)palladium intermediate.
Butler
DC
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Inman
GA
Alper
H