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Ligand and reaction development in the Rhodium(III)-catalyzed C-H activation-mediated synthesis of n-heterocycles

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dc.contributor.authorHyster, Todd K., author
dc.contributor.authorRovis, Tomislav, advisor
dc.contributor.authorFinke, Richard G., committee member
dc.contributor.authorChen, Eugene Y.-X., committee member
dc.contributor.authorBailey, Travis S., committee member
dc.contributor.authorKanatous, Shane B., committee member
dc.date.accessioned2007-01-03T05:53:45Z
dc.date.available2007-01-03T05:53:45Z
dc.date.issued2013
dc.description.abstractDescribed herein are the development of new directing groups and new ligands for Rh(III)- catalyzed, multi-component synthesis of nitrogen containing heterocycles. The amide directing group was found to be an effective coupling partner for the synthesis of isoquinolones. Mechanistic experiments suggested the possibility to activated alkenyl C-H bonds for the synthesis of pyridones. During these studies, development of a new cyclopentadienyl ligand (Cpt) for C-H activation allowed for enhanced regioselectivity in the alkyne insertion event. Oxime directing groups were found to provide pyridines when coupled with alkynes. Again the Cpt ligand impacted the alkyne migratory insertion event. This ligand is also effective in controlling the migratory insertion of alkenes in the synthesis of dihydroisoquinolones. An enantioselective synthesis of dihydroisoquinolones was discovered using a strept(avidin)-based artificial metalloenzyme providing enhanced reactivity, regioselectivity, and enantioselectivity. This artificial metalloenzyme is also effective for controlling the enantioselective synthesis of γ-lactams from diazo compounds and benzamides.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierHyster_colostate_0053A_11873.pdf
dc.identifier.urihttp://hdl.handle.net/10217/80154
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2000-2019
dc.rightsCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.
dc.subjectC-H activation
dc.subjectrhodium
dc.subjectmetalloenzyme
dc.subjectcyclopentadienyl ligand
dc.titleLigand and reaction development in the Rhodium(III)-catalyzed C-H activation-mediated synthesis of n-heterocycles
dc.typeText
dcterms.rights.dplaThis Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

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