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

Abstract

AbstractN‐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.