Palladium-catalyzed elimination reactions of stereodefined enol triflates

dc.contributor.advisorFrantz, Doug E.
dc.contributor.authorCrouch, Ian T.
dc.contributor.committeeMemberNegrete, George
dc.contributor.committeeMemberMusie, Ghezai
dc.contributor.committeeMemberZhao, John
dc.date.accessioned2024-02-09T20:18:59Z
dc.date.available2024-02-09T20:18:59Z
dc.date.issued2013
dc.descriptionThis item is available only to currently enrolled UTSA students, faculty or staff. To download, navigate to Log In in the top right-hand corner of this screen, then select Log in with my UTSA ID.
dc.description.abstractThe following dissertation will describe palladium-catalyzed reactions of stereodefined enol triflates, which are readily accessible from the corresponding ß-ketoesters. Both 2,4- dienoate esters and chiral allenic esters are highly referenced synthetic intermediates. Through manipulation of reaction conditions, a general procedure for obtaining 2,4-dienoate esters from either [Z]- or [E]- enol triflates is presented. Using a chiral palladium catalyst, a highly enantioselective synthesis of allenic esters is demonstrated, which is proposed to proceed through a mechanism involving enantioselective ß-hydride elimination. The development of novel chiral ligands for this purpose is put forth. This methodology is applied to a formal total synthesis of the natural product (+) epibatidine.
dc.description.departmentChemistry
dc.format.extent361 pages
dc.format.mimetypeapplication/pdf
dc.identifier.isbn9781303391033
dc.identifier.urihttps://hdl.handle.net/20.500.12588/3128
dc.languageen
dc.subjectallene
dc.subjectbeta-hydride
dc.subjectelimination
dc.subjectenantioselective
dc.subjectpalladium
dc.subjecttriflate
dc.subject.classificationOrganic chemistry
dc.titlePalladium-catalyzed elimination reactions of stereodefined enol triflates
dc.typeThesis
dc.type.dcmiText
dcterms.accessRightspq_closed
thesis.degree.departmentChemistry
thesis.degree.grantorUniversity of Texas at San Antonio
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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