Synthetic studies of N-heterocycles via catalytic reductive C-C bond formation and tertiary neopentyl substitution

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dc.contributor.advisorKrische, Michael J.en
dc.contributor.committeeMemberMartin, Stephen F.en
dc.contributor.committeeMemberSiegel, Dionicio R.en
dc.contributor.committeeMemberBrodbelt, Jennifer S.en
dc.contributor.committeeMemberKerwin, Sean M.en
dc.creatorGrant, Christopher Donalden
dc.date.accessioned2012-07-06T17:55:36Zen
dc.date.accessioned2017-05-11T22:25:40Z
dc.date.available2012-07-06T17:55:36Zen
dc.date.available2017-05-11T22:25:40Z
dc.date.issued2012-05en
dc.date.submittedMay 2012en
dc.date.updated2012-07-06T17:56:24Zen
dc.descriptiontexten
dc.description.abstractWhilst there are a large number of C-C bond forming reactions available for the construction of heterocycles a number of these protocols require the use of stoichiometric organometallic reagents. Since heterocycles are present in the vast majority of pharmaceutical agents the ability to forge these structures efficiently with a minimal amount of stoichiometric metallic waste is important. With this in mind we initiated a series of projects that focus on the use of [pi]-unsaturates to serve as surrogates to toxic, air and moisture sensitive nucleophilic organometallic reagents utilized in traditional C-C bond forming reactions. This has allowed us to develop catalytic couplings of vinyl azines to imines to form branched amines, to couplings of dimethylallene to isatin forming a tert-prenyl hydroxy oxindole and this neopentyl alcohol can be substituted with C-nucleophiles forming two contiguous quaternary all-carbon centers in our synthetic studies tert-prenyl indole alkaloid natural products.en
dc.description.departmentChemistryen
dc.format.mimetypeapplication/pdfen
dc.identifier.slug2152/ETD-UT-2012-05-5084en
dc.identifier.urihttp://hdl.handle.net/2152/ETD-UT-2012-05-5084en
dc.language.isoengen
dc.subjectCatalyticen
dc.subjectHeterocycleen
dc.subjectNeopentyl substitutionen
dc.subjectSynthesisen
dc.titleSynthetic studies of N-heterocycles via catalytic reductive C-C bond formation and tertiary neopentyl substitutionen
dc.title.alternativeSynthetic studies of N-heterocycles via catalytic reductive C-C bond coupling and tertiary neopentyl substitutionen
dc.type.genrethesisen

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