Lewis acid catalyzed diastereoselective cycloaddition reactions of Donor-Acceptor cyclopropanes and vinyl azides: synthesis of functionalized azidocyclopentane and tetrahydropyridine derivatives

Abstract

Lewis acid catalyzed [3 + 2]-cycloaddition reaction of donor−acceptor cyclopropanes with vinyl azides has been developed to obtain diastereomerically enriched azidocyclopentane derivatives. In addition, thermal chemoselective ring expansion of azidocyclopentanes to tetrahydropyridine derivatives and further diastereospecific reduction to a substituted piperidine derivative, with an excellent yield, was also achieved.