Functionalization of 4-Substituted Pyridines for Enantioselective Synthesis

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dc.contributor.advisorGarcia, Josue Arturo Orellana
dc.contributor.authorHunter, Isabelle Anne Carriere
dc.date.accessioned2021-07-06T12:39:39Z
dc.date.available2021-07-06T12:39:39Z
dc.date.copyright2020-07
dc.date.issued2021-07-06
dc.date.updated2021-07-06T12:39:38Z
dc.degree.disciplineChemistry
dc.degree.levelMaster's
dc.degree.nameMSc - Master of Science
dc.description.abstractEnantioselective synthesis using nitrogen containing heterocycles, such as pyridines, is extremely useful in drug discovery. The prevalence of pyridines in the drug market is well-documented and a mild, enantioselective method to functionalize pyridines would allow faster access to more structurally diverse pyridines, improving efficiency in the search of drug candidates. The Orellana group has developed a strategy for selective allylation of 4-substituted pyridines using mild conditions, which results in broad functional group tolerance. Reported herein are ways to expand the allyl fragment to larger linear and cyclic fragments, and attempts at the development of an enantioselective variant using palladium catalyzed decarboxylative allylation. The pathway for reductive elimination was also discovered through mechanistic experiments which revealed more of this palladium catalyzed decarboxylative allylation mechanism. Furthermore, a new method was investigated for arylation of the pyridylic position using a high-valent copper catalysis.
dc.identifier.urihttp://hdl.handle.net/10315/38417
dc.languageen
dc.rightsAuthor owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
dc.subjectOrganic chemistry
dc.subject.keywordschemistry
dc.subject.keywordsorganic chemistry
dc.subject.keywordssynthesis
dc.subject.keywordsenantioselectivity
dc.subject.keywordspyridines
dc.subject.keywordsallylation
dc.subject.keywordspalladium
dc.subject.keywordscopper
dc.subject.keywordsmild synthesis
dc.subject.keywordsfunctionalization
dc.subject.keywordsheterocycle
dc.subject.keywordsenantioselective
dc.subject.keywordspyridine
dc.subject.keywordsmild conditions
dc.titleFunctionalization of 4-Substituted Pyridines for Enantioselective Synthesis
dc.typeElectronic Thesis or Dissertation

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