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Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Yan, Qiao; Bolte, Benoit; Bai, Yuhua; Banwell, Martin; Willis, Anthony; Carr, Paul D

Description

A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels–Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.

dc.contributor.authorYan, Qiao
dc.contributor.authorBolte, Benoit
dc.contributor.authorBai, Yuhua
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.contributor.authorCarr, Paul D
dc.date.accessioned2019-04-08T04:21:31Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/159303
dc.description.abstractA series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels–Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.
dc.description.sponsorshipWe thank the Australian Research Council and the Institute of Advanced Studies for financial support. Q.Y. is the grateful recipient of a CSC PhD Scholarship provided by the Government of the People’s Republic of China.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.rights© 2017 American Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleStudies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume82
dc.date.issued2017
local.identifier.absfor030606 - Structural Chemistry and Spectroscopy
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationa383154xPUB8309
local.publisher.urlhttps://pubs.acs.org/
local.type.statusPublished Version
local.contributor.affiliationYan, Qiao, College of Science, ANU
local.contributor.affiliationBolte, Benoit, College of Science, ANU
local.contributor.affiliationBai, Yuhua, College of Science, ANU
local.contributor.affiliationBanwell, Martin, College of Science, ANU
local.contributor.affiliationWillis, Anthony, College of Science, ANU
local.contributor.affiliationCarr, Paul D, College of Science, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue15
local.bibliographicCitation.startpage8008
local.bibliographicCitation.lastpage8022
local.identifier.doi10.1021/acs.joc.7b01243
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2019-03-12T07:21:04Z
local.identifier.scopusID2-s2.0-85027041832
local.identifier.thomsonID000407307700030
CollectionsANU Research Publications

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