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dc.contributor.advisorLam, Hon Wai
dc.contributor.authorOswald, Claire Louise
dc.date.accessioned2011-01-18T11:57:41Z
dc.date.available2011-01-18T11:57:41Z
dc.date.issued2010
dc.identifier.urihttp://hdl.handle.net/1842/4614
dc.description.abstractHydrometalation of α,β-unsaturated carbonyl compounds provides access to reactive metal enolates, which can then be trapped by a suitable electrophile. The coppercatalysed reductive aldol reaction involves hydrometalation of an α,β-unsaturated carbonyl compound, followed by an inter- or intramolecular aldol reaction. While there have been numerous examples of copper-catalysed reductive aldol reactions reported in the literature, the corresponding reductive Michael reaction has been relatively understudied. Herein, the copper-catalysed reductive Michael cyclisation of substrates containing two α,β-unsaturated carbonyl moieties is described. A range of structurally and electronically diverse substrates were prepared by various different methods. Both α,β-unsaturated ketones and esters underwent cyclisation, in the presence of a copper catalyst, a bisphosphine ligand, and a stoichiometric reductant, to afford 5- and 6- membered carbocyclic and heterocyclic products, with good-to-excellent levels of diastereo- and enantiocontrol. Furthermore, the diastereochemical outcome of these reactions is dependent on the specific reaction conditions used.en
dc.language.isoenen
dc.publisherThe University of Edinburghen
dc.subjectMichael reactionen
dc.subjectketones (benzene compounds)en
dc.titleEnantioselective copper-catalysed reductive Michael cyclisationsen
dc.typeThesis or Dissertationen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD Doctor of Philosophyen


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