Synthesis of spirocyclic heterocycles from α,β-unsaturated N -acyliminium ions

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dc.contributor.authorThaima, Thanaphat
dc.contributor.authorYazici, Arife
dc.contributor.authorAuranwiwat, Chiramet
dc.contributor.authorWillis, Anthony
dc.contributor.authorWille, Uta
dc.contributor.authorLimtharakul, Thunwadee
dc.contributor.authorPyne, Stephen G
dc.date.accessioned2024-03-04T00:34:08Z
dc.date.issued2021
dc.date.updated2022-10-16T07:25:56Z
dc.description.abstractThe reactions of α,β-unsaturated N-acyliminium ions, generated in situ from 4(S)-O-substitutedhydroxy5-hydroxy-5-vinyl-N-alkylpyrrolidin-2-ones, with allylsilanes and indoles leading to the formation of spirocyclic heterocycles, are reported. Six single crystal X-ray structures and extensive 2D NMR experiments confirmed the structures and stereochemistries of these products. In addition, computational studies provided mechanistic insights and an understanding of the stereochemical outcomes of these reactions.en_AU
dc.description.sponsorshipAnalytiCon Discovery GmbH, Germany, and the Universities of Wollongong (SMAH Research Partnership Grant) and Melbourne (High Performance Computing service) for their support.en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn1477-0520en_AU
dc.identifier.urihttp://hdl.handle.net/1885/315657
dc.language.isoen_AUen_AU
dc.publisherRoyal Society of Chemistryen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP130101968en_AU
dc.rights© 2021 The authorsen_AU
dc.sourceOrganic and Biomolecular Chemistryen_AU
dc.titleSynthesis of spirocyclic heterocycles from α,β-unsaturated N -acyliminium ionsen_AU
dc.typeJournal articleen_AU
local.bibliographicCitation.issue1en_AU
local.bibliographicCitation.lastpage272en_AU
local.bibliographicCitation.startpage259en_AU
local.contributor.affiliationThaima, Thanaphat, University of Wollongongen_AU
local.contributor.affiliationYazici, Arife, University of Wollongongen_AU
local.contributor.affiliationAuranwiwat, Chiramet, Chiang Mai Universityen_AU
local.contributor.affiliationWillis, Anthony, College of Science, ANUen_AU
local.contributor.affiliationWille, Uta, University of Melbourneen_AU
local.contributor.affiliationLimtharakul, Thunwadee, Chiang Mai Universityen_AU
local.contributor.affiliationPyne, Stephen G, University of Wollongongen_AU
local.contributor.authoruidWillis, Anthony, u8512028en_AU
local.description.embargo2099-12-31
local.description.notesImported from ARIESen_AU
local.identifier.absfor340503 - Organic chemical synthesisen_AU
local.identifier.ariespublicationa383154xPUB17332en_AU
local.identifier.citationvolume19en_AU
local.identifier.doi10.1039/d0ob02075cen_AU
local.identifier.scopusID2-s2.0-85099134223
local.identifier.thomsonIDWOS:000607351800022
local.publisher.urlhttps://pubs.rsc.org/en_AU
local.type.statusPublished Versionen_AU

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