The diastereoselective synthesis and reactions of beta-azido vinyl esters from enol triflates

dc.contributor.advisorFrantz, Doug E.
dc.contributor.authorRuiz, Francisco Xavier, II
dc.contributor.committeeMemberTonzetich, Zachary J.
dc.contributor.committeeMemberLarionov, Oleg
dc.date.accessioned2024-02-12T20:02:42Z
dc.date.available2024-02-12T20:02:42Z
dc.date.issued2012
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 diastereoselective synthesis of beta-azido vinyl esters is presented. Using stereodefined enol triflates developed in the Frantz lab, highly substituted (E/Z)-vinyl azides are accessed by performing conjugate additions of sodium azide with the corresponding (E/Z)-enol triflate in DMF to yield the desired azide in stereoselective fashion. Further investigation of these vinyl azides demonstrates their ability to exhibit differential reactivity leading to various heterocycles. When (E/Z)-vinyl azides are exposed to heat, the formation of a nitrene intermediate occurs. By strategically providing various substitution patterns on these nitrene intermediates, a pathway to specific heterocycles including azirines, isoxazoles, and pyrroles is feasible.
dc.description.departmentChemistry
dc.format.extent82 pages
dc.format.mimetypeapplication/pdf
dc.identifier.isbn9781267843371
dc.identifier.urihttps://hdl.handle.net/20.500.12588/5379
dc.languageen
dc.subjectazido vinyl ester
dc.subjectdiastereoselective
dc.subjectenol triflate
dc.subjectsynthesis
dc.subject.classificationOrganic chemistry
dc.titleThe diastereoselective synthesis and reactions of beta-azido vinyl esters from enol triflates
dc.typeThesis
dc.type.dcmiText
dcterms.accessRightspq_closed
thesis.degree.departmentChemistry
thesis.degree.grantorUniversity of Texas at San Antonio
thesis.degree.levelMasters
thesis.degree.nameMaster of Science

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