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dc.contributor.authorMoynihan, Lorna
dc.contributor.authorChadda, Rekha
dc.contributor.authorMcArdle, Patrick
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2016-08-10T08:57:18Z
dc.date.issued2015-12-09
dc.identifier.citationMoynihan, 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.5b03209en_IE
dc.identifier.issn1523-7052
dc.identifier.urihttp://hdl.handle.net/10379/5941
dc.description.abstractAllylic 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.en_IE
dc.description.sponsorshipThis research was supported by the Irish Research Council (Ph.D. scholarship to L.M.) and NUI Galway (College of Science Ph.D. scholarship to R.C.). This publication has also emanated in part from research supported by Science Foundation Ireland (SFI, 07/IN.1/B966) that was cofunded under the European Regional Development Fund.en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherAmerican Chemical Societyen_IE
dc.relation.ispartofOrganic Lettersen
dc.subjectChemistryen_IE
dc.subjectInhibitionen_IE
dc.subjectTransformationsen_IE
dc.subjectMechanismen_IE
dc.titleAllylic azide rearrangement in tandem with Huisgen cycloaddition for stereoselective annulation: synthesis of C-Glycosyl iminosugarsen_IE
dc.typeArticleen_IE
dc.date.updated2016-08-09T11:28:40Z
dc.identifier.doi10.1021/acs.orglett.5b03209
dc.local.publishedsourcehttp:/dx.doi.org/10.1021/acs.orglett.5b03209en_IE
dc.description.peer-reviewedpeer-reviewed
dc.description.embargo2016-12-09
dc.internal.rssid10467047
dc.local.contactPaul Murphy, School Of Chemistry, Room 236, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedNo
dc.local.versionACCEPTED
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