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
Description
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.author | Nugent, Jeremy | |
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dc.contributor.author | Matoušová, Eliška | |
dc.contributor.author | Banwell, Martin | |
dc.contributor.author | Willis, Anthony | |
dc.date.accessioned | 2021-01-06T04:29:38Z | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.uri | http://hdl.handle.net/1885/219196 | |
dc.description.abstract | 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.description.sponsorship | We [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.mimetype | application/pdf | |
dc.language.iso | en_AU | |
dc.publisher | American Chemical Society | |
dc.rights | © 2017 American Chemical Society | |
dc.source | Journal of Organic Chemistry | |
dc.title | The Palladium-Catalyzed Intramolecular Alder-Ene Reactions of O- and N-Linked 1,6-Enynes Incorporating Triethylsilyl Capping Groups | |
dc.type | Journal article | |
local.description.notes | Imported from ARIES | |
local.identifier.citationvolume | 82 | |
dc.date.issued | 2017 | |
local.identifier.absfor | 030502 - Natural Products Chemistry | |
local.identifier.ariespublication | a383154xPUB8977 | |
local.publisher.url | http://pubs.acs.org/journal/joceah/about.html | |
local.type.status | Published Version | |
local.contributor.affiliation | Nugent, Jeremy, College of Science, ANU | |
local.contributor.affiliation | Matousova, Eliska, College of Science, ANU | |
local.contributor.affiliation | Banwell, Martin, College of Science, ANU | |
local.contributor.affiliation | Willis, Anthony, College of Science, ANU | |
local.description.embargo | 2037-12-31 | |
dc.relation | http://purl.org/au-research/grants/arc/DP170100926 | |
local.bibliographicCitation.issue | 23 | |
local.bibliographicCitation.startpage | 12569 | |
local.bibliographicCitation.lastpage | 12589 | |
local.identifier.doi | 10.1021/acs.joc.7b02355 | |
dc.date.updated | 2020-11-23T11:19:10Z | |
local.identifier.scopusID | 2-s2.0-85036620614 | |
Collections | ANU Research Publications |
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