Enantioselective transformations of α-diazocarbonyl compounds; catalyst and substrate effects

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dc.check.date10000-01-01
dc.check.embargoformatBoth hard copy thesis and e-thesisen
dc.check.entireThesisEntire Thesis Restricted
dc.check.infoIndefiniteen
dc.check.opt-outNot applicableen
dc.check.reasonThis thesis is due for publication or the author is actively seeking to publish this materialen
dc.contributor.advisorMaguire, Anita R.en
dc.contributor.authorRing, Aoife
dc.contributor.funderHigher Education Authorityen
dc.contributor.funderCork County Councilen
dc.date.accessioned2017-06-01T12:51:17Z
dc.date.issued2016
dc.date.submitted2016
dc.description.abstractThe primary objective of this thesis was an extensive investigation into transition metal catalysed intramolecular C–H insertion reactions of α-diazoacetamides and intramolecular aromatic addition reactions of α-diazoketones. Exploration of the effect of substrate structure and the impact of various aspects of the catalyst complex was undertaken to determine which has a greater influence on the ensuing C–H insertion and aromatic addition reactions. While particular attention was paid to copper-bisoxazoline catalyst complexes, studies were also conducted, although to a lesser extent, using the more widely studied achiral and chiral rhodium catalysts. Significantly, use of the copper complexes in C–H insertion reactions of α-diazoacetamides resulted in formation of γ-lactams and β-lactams in high enantiopurities, 91% ee and 83% ee, while copper catalysed aromatic addition reactions resulted in formation of azulenones in up to 92% ee.en
dc.description.sponsorshipHigher Education Authority (PRTLI4)en
dc.description.statusNot peer revieweden
dc.description.versionAccepted Version
dc.format.mimetypeapplication/pdfen
dc.identifier.citationRing, A. 2016. Enantioselective transformations of α-diazocarbonyl compounds; catalyst and substrate effects. PhD Thesis, University College Cork.en
dc.identifier.endpage451en
dc.identifier.urihttps://hdl.handle.net/10468/4036
dc.language.isoenen
dc.publisherUniversity College Corken
dc.rights© 2016, Aoife Ring.en
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subjectC-H insertionen
dc.subjectCopper catalysisen
dc.subjectDiazocarbonylen
dc.subjectLactamsen
dc.subjectSulfonesen
dc.subjectBuchner reactionen
dc.subjectRhodium catalysisen
dc.subjectEnantioselectiveen
dc.subjectBisoxazolineen
dc.thesis.opt-outfalse
dc.titleEnantioselective transformations of α-diazocarbonyl compounds; catalyst and substrate effectsen
dc.typeDoctoral thesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD (Science)en
ucc.workflow.supervisora.maguire@ucc.ie
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