Intermolecular 1,3-Dipolar Cycloaddition Reaction of N-Carbamoyl Nitrones Generated by N-Selective Carbamoylation of Oximes with Isocyanates

Abstract

N-Selective carbamoylation reaction of oximes with isocyanates generates nitrones, which undergo 1,3-dipolar cycloaddition with various dipolarophiles to afford diverse isoxazolidines. Notably, combinations of highly electron-rich oxime and highly electron-deficient dipolarophile exhibited high reactivity, with product yields of up to 94 %. The substituent on the isoxazolidine-nitrogen atom could be successfully removed without loss of the cyclic structure. Computational studies have also elucidated the mechanism of the reaction and origin of stereoselectivity.

Keywords: cycloaddition; heterocycles; isocyanate; multicomponent reactions; nitrone.