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The Palladium-Catalyzed Intramolecular Alder-Ene Reactions of O- and N-Linked 1,6-Enynes Incorporating Triethylsilyl Capping Groups

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Nugent, Jeremy; Matoušová, Eliška; Banwell, Martin; Willis, Anthony

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A series of O- and N-linked 1,6-enynes (e.g., 11) have been prepared with each subjected to a palladium-catalyzed intramolecular Alder-ene (IMAE) reaction, thus producing the isomeric and cyclic 1,4-diene (e.g., 12). These processes proceed most effectively when a triethylsilyl group is attached to the alkyne moiety and so generating alkenylsilanes that can be manipulated in various useful ways, including via iododesilylation (to give, for example, iodoalkene 62).

dc.contributor.authorNugent, Jeremy
dc.contributor.authorMatoušová, Eliška
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.date.accessioned2021-01-06T04:29:38Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/219196
dc.description.abstractA series of O- and N-linked 1,6-enynes (e.g., 11) have been prepared with each subjected to a palladium-catalyzed intramolecular Alder-ene (IMAE) reaction, thus producing the isomeric and cyclic 1,4-diene (e.g., 12). These processes proceed most effectively when a triethylsilyl group is attached to the alkyne moiety and so generating alkenylsilanes that can be manipulated in various useful ways, including via iododesilylation (to give, for example, iodoalkene 62).
dc.description.sponsorshipWe [thank] the Australian Research Council and the Institute of Advanced Studies for financial support. J.N. is the grateful recipient of a PhD Scholarship provided by the Australian Government.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.rights© 2017 American Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleThe Palladium-Catalyzed Intramolecular Alder-Ene Reactions of O- and N-Linked 1,6-Enynes Incorporating Triethylsilyl Capping Groups
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume82
dc.date.issued2017
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.ariespublicationa383154xPUB8977
local.publisher.urlhttp://pubs.acs.org/journal/joceah/about.html
local.type.statusPublished Version
local.contributor.affiliationNugent, Jeremy, College of Science, ANU
local.contributor.affiliationMatousova, Eliska, College of Science, ANU
local.contributor.affiliationBanwell, Martin, College of Science, ANU
local.contributor.affiliationWillis, Anthony, College of Science, ANU
local.description.embargo2037-12-31
dc.relationhttp://purl.org/au-research/grants/arc/DP170100926
local.bibliographicCitation.issue23
local.bibliographicCitation.startpage12569
local.bibliographicCitation.lastpage12589
local.identifier.doi10.1021/acs.joc.7b02355
dc.date.updated2020-11-23T11:19:10Z
local.identifier.scopusID2-s2.0-85036620614
CollectionsANU Research Publications

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