Intramolecular [3 + 2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds

Abstract

A regio and diastereoselective strategy has been developed for the synthesis of complex bicyclo[3.2.1]octane scaffolds from the reaction of readily accessible vinylogous carbonates with N-substituted hydroxylamine hydrochlorides via intramolecular 1,3-dipolar nitrone cycloaddition reaction. Wide varieties of bicyclic isoxazolidines were synthesized in high yields under catalyst free conditions through a highly efficient and operationally simple protocol.