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dc.contributor.advisorConnon, Stephen
dc.contributor.authorCRAIG, RYAN
dc.date.accessioned2018-09-26T19:53:10Z
dc.date.available2018-09-26T19:53:10Z
dc.date.submitted2018
dc.identifier.citationCRAIG, RYAN, Development of Enantioselective Processes Catalysed by Novel Asymmetric Bifunctional Phase-Transfer Organocatalysts, Trinity College Dublin. School of Chemistry.CHEMISTRY, 2018en
dc.identifier.urihttp://hdl.handle.net/2262/85033
dc.description.abstractA new family of chiral bifunctional phase-transfer catalysts were developed to promote an enantioselective SN2 reaction for the construction of malleable oxindoles with all-carbon quaternary stereocenters in high yield and excellent enantioselectivity (up to 97% ee). The utility of this methodology was demonstrated through the concise and highly enantioselective synthesis of (-)-debromoflustramine B and (-)-flustramine B. The newly developed family of chiral bifunctional phase-transfer catalysts, in conjunction with catalytic amounts of fluoride, were also utilised in a hitherto, unprecedented method of enantiocontrolled desymmetrisation. A selection of meso-anhydrides were converted to their corresponding hemiesters with reasonable levels of enantiocontrol. Reaction scope was demonstrated with the promotion of a nucleophilic catalysis-mediated rearrangement of O-acylated enolates as well as a nucleophilic catalysis-mediated Curtius rearrangement to form synthetically useful productsen
dc.language.isoenen
dc.subjectAlkylationen
dc.subjectEnolatesen
dc.subjectOxindolesen
dc.subjectPhase-transfer catalysisen
dc.subjectPyrroloindolineen
dc.subjectDesymmetrisationen
dc.subjectAcyl-transferen
dc.subjectNucleophillic fluoride catalysisen
dc.titleDevelopment of Enantioselective Processes Catalysed by Novel Asymmetric Bifunctional Phase-Transfer Organocatalystsen
dc.typeThesisen
dc.contributor.sponsorScience Foundation Irelanden
dc.contributor.sponsorScience Foundation Irelanden
dc.publisher.institutionTrinity College Dublin, School of Chemistry, CHEMISTRYen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhDen
dc.rights.ecaccessrightsopenAccess
dc.contributor.sponsorGrantNumber12-IA-1645en
dc.contributor.sponsorGrantNumber12\RC\2275en


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