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N-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids

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dc.contributor.authorVora, Harit, author
dc.contributor.authorRovis, Tomislav, advisor
dc.contributor.authorWilliams, Robert, committee member
dc.contributor.authorWood, John, committee member
dc.contributor.authorChen, Eugene, committee member
dc.contributor.authorMcNeil, Michael, committee member
dc.date.accessioned2007-01-03T05:49:54Z
dc.date.available2007-01-03T05:49:54Z
dc.date.issued2011
dc.description.abstractN-heterocyclic carbene catalyzed α-redox reaction has been utilized towards the catalytic synthesis of amides utilizing amines and substoichiometric quantities of an acyl transfer reagent in a waste reduced acylation process. The reaction is amenable to a plethora of amines and amine hydrochloride salts as nucleophiles. The reaction is applicable towards a variety α-reducible aldehydes as α,α-dichloro aldehydes, enals, epoxy and aziridnyl aldehydes all provide the respective amides in moderate to excellent yields with the latter in high diastereoselectivity. The asymmetric amidation reaction provides chiral amides in moderate enantioselectivity. Additionally, the N-heterocyclic carbene catalyzed α-redox reaction was also utilized for the synthesis of enantioenriched α-chloro and α-fluoro carboxylic acids. The reaction also provide for a mild installation of a deuterium from D2O furnishing enantioenriched isotopically labeled compounds. Investigations in to the mechanism have revealed that the carbene displays behavior of a phase transfer reagent by shuttling hydroxide from the aqueous phase to the organic phase. Additionally, it has been found that the turnover limiting step in this acylation process in the hydrolysis of the acyl azolium.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierVora_colostate_0053A_10679.pdf
dc.identifier.urihttp://hdl.handle.net/10217/52114
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.subjectsynthesis
dc.subjectNHC catalysis
dc.subjectorganic chemistry
dc.subjectasymmetric
dc.subjectcatalysis
dc.titleN-heterocyclic carbene catalyzed α-redox reaction: catalytic synthesis of amides and carboxylic acids
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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