The Use of Chiral Dihydropyridones in the Development of Novel Synthetic Methodology

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dc.contributor.advisorDr. John Cavanagh, Committee Memberen_US
dc.contributor.advisorDr. Christian Corey Melander, Committee Memberen_US
dc.contributor.advisorDr. Daniel Comins, Committee Chairen_US
dc.contributor.advisorDr. Thomas Brent Gunnoe, Committee Memberen_US
dc.contributor.advisorDr. Jon S Lindsey, Committee Memberen_US
dc.contributor.authorMcCall, W. Stephen Jr.en_US
dc.date.accessioned2010-04-02T19:13:55Z
dc.date.available2010-04-02T19:13:55Z
dc.date.issued2007-11-09en_US
dc.degree.disciplineChemistryen_US
dc.degree.leveldissertationen_US
dc.degree.namePhDen_US
dc.description.abstractA chiral ligand was synthesized using an enantiopure dihydropyridone as starting material. The ligand was tested for efficacy in the diethyl zinc aldehyde addition reaction, giving poor chiral induction. The von Braun tertiary amine cleavage reaction was used to regio and stereoselectively ring open chiral piperidines with varying degrees of substitution. The mechanistic course of the reaction was investigated and postulated. A new silyl assisted (SivB) version of the von Braun reaction was discovered. This was utilized to open piperidines to give a terminal alkene as a useful synthetic handle remaining in the molecule.en_US
dc.identifier.otheretd-08092007-182313en_US
dc.identifier.urihttp://www.lib.ncsu.edu/resolver/1840.16/5440
dc.rightsI hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dis sertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to NC State University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report.en_US
dc.subjectAmine cleavageen_US
dc.subjectvon Bruanen_US
dc.subjectHeterocyclesen_US
dc.subjectDihydropyridoneen_US
dc.titleThe Use of Chiral Dihydropyridones in the Development of Novel Synthetic Methodologyen_US

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