Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor–Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives

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.