Allylic azide rearrangement in tandem with Huisgen cycloaddition for stereoselective annulation: synthesis of C-Glycosyl iminosugars
Murphy, Paul V.
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Moynihan, Lorna, Chadda, Rekha, McArdle, Patrick, & Murphy, Paul V. (2015). Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars. Organic Letters, 17(24), 6226-6229. doi: 10.1021/acs.orglett.5b03209
Allylic azide rearrangement is used. in,tandem with. intramolecular azide-alkene cycloaddition to give a triazoline that when subsequently decomposed in the presence of a nucleophile gives piperidines. The tandem reaction gives two stereocenters that are generated With high control. The formation of-the piperidines required the presence of innate conformational constraint. The-applicability of the annulation reaction is demonstrated by the synthesis iminosugars. A proposal is included to account for the observed stereoselectivity, which is influenced by the precursor structure.