title: Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars.
abstract: 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 of iminosugars. A proposal is included to account for the observed stereoselectivity, which is influenced by the precursor structure.
authors.affiliation: School of Chemistry, National University of Ireland Galway , University Road, Galway, Ireland.
authors.forename: Lorna
authors.initials: L
authors.lastname: Moynihan
authors.affiliation: School of Chemistry, National University of Ireland Galway , University Road, Galway, Ireland.
authors.forename: Rekha
authors.initials: R
authors.lastname: Chadda
authors.affiliation: School of Chemistry, National University of Ireland Galway , University Road, Galway, Ireland.
authors.forename: Patrick
authors.initials: P
authors.lastname: McArdle
authors.affiliation: School of Chemistry, National University of Ireland Galway , University Road, Galway, Ireland.
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D050112:Imino Pyranoses / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001386:Azides; D006027:Glycosides; D050112:Imino Pyranoses; D010880:Piperidines