Metal-Catalyzed Transformations of Stereodefined Enol Triflates and Their Derivatives

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dc.contributor.advisorFrantz, Doug E.
dc.contributor.authorEl Arba, Marie E.
dc.contributor.committeeMemberMcHardy, Stanton F.
dc.contributor.committeeMemberDoyle, Michael P.
dc.contributor.committeeMemberLarionov, Oleg V.
dc.date.accessioned2024-02-09T20:48:58Z
dc.date.available2024-02-09T20:48:58Z
dc.date.issued2018
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 metal-catalyzed transformations of stereodefined enol triflates and their derivatives. Enol triflates are widely versatile synthetic building blocks in organic chemistry. This dissertation will demonstrate their utility by disclosing methods for the synthesis of racemic allenoates, fully substituted furans and γ-butenolides. The first method describes a robust synthesis of racemic allenoates via a palladium-catalyzed β-hydride elimination of (E)-enol triflates. This procedure accesses all four patterns of substituted allenoates from a single substrate class. The second method presents a mild synthesis of tri- and tetra-substituted furans via a ruthenium-catalyzed cyclization of diazoacetates, reagents derived from (Z)-enol triflates. This work also demonstrates the synthetic utility of substituted furans by obtaining butenolides through a highly regioselective method under mild acidic conditions. Finally, the third method utilizes the newly developed furans to accomplish a palladium-catalyzed benzylic migration of these substrates to yield γ-butenolides possessing a quaternary center.
dc.description.departmentChemistry
dc.format.extent271 pages
dc.format.mimetypeapplication/pdf
dc.identifier.isbn9780355957723
dc.identifier.urihttps://hdl.handle.net/20.500.12588/3319
dc.languageen
dc.subject.classificationOrganic chemistry
dc.titleMetal-Catalyzed Transformations of Stereodefined Enol Triflates and Their Derivatives
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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