Lewis Acid Catalyzed Diastereoselective Cycloaddition Reactions of Donor–Acceptor Cyclopropanes and Vinyl Azides: Synthesis of Functionalized Azidocyclopentane and Tetrahydropyridine Derivatives
datasetposted on 03.01.2017, 17:10 by Raghunath Dey, Prabal Banerjee
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.
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chemoselective ring expansionCyclopropaneDonorcycloadditionpiperidinedonorSynthesitetrahydroazidocyclocyclopropanederivativevinyl azidesVinyl AzidesFunctionalized Azidocyclopentanediastereomericallydiastereospecific reductionCatalyzed Diastereoselective Cycloaddition ReactionsTetrahydropyridine Derivatives Lewis acid