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Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions

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dc.contributor.authorDalton, Derek M., author
dc.contributor.authorRovis, Tomislav, advisor
dc.contributor.authorWood, John L., committee member
dc.contributor.authorKennan, Alan J., committee member
dc.contributor.authorRappé, Anthony K., committee member
dc.contributor.authorSnow, Christopher D., committee member
dc.date.accessioned2007-01-03T05:53:40Z
dc.date.available2007-01-03T05:53:40Z
dc.date.issued2013
dc.description.abstractDescribed herein are mechanistic studies and ligand development for Rh(I) catalyzed [2+2+2] cycloaddition reactions of alkene tethered isocyanates and exogenous alkynes. A mechanistic hypothesis has been proposed and supported through experiment. Novel perfluoroaryl Taddol phosphoramidite ligands were developed based on the mechanistic hypothesis. Improvements in product and enantioselectivity were found using the perfluoroaryl Taddol phosphoramidite ligand, CKphos. This catalyst system was studied by NMR, X-ray and DFT calculations. Rh(I)-C6F5 and Co(-1)-C6F5 interactions were found in the course of studying the CKphos catalysts. The Rh-CKphos catalyst system was used in the synthesis of the tricyclic core structure of the cylindricine and lepadiformine alkaloids. Finally a Zn(II)-catalyzed [4+2] cycloaddition of 1- azabutadienes and nitro olefins was discovered and developed as an efficient and selective means to synthesize tetrahydropyridines.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierDalton_colostate_0053A_11811.pdf
dc.identifier.urihttp://hdl.handle.net/10217/80142
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.subjectcycloaddition
dc.subjectzinc
dc.subjectrhodium
dc.subjectenantioselective
dc.subjectheterocycles
dc.subjectcatalysis
dc.titleMechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions
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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