Catalytic methods for the synthesis of spirooxindoles, pyrroloindolines, and flavanones

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dc.contributor.advisor Levi M. Stanley
dc.contributor.author Gerten, Anthony
dc.contributor.department Chemistry
dc.date 2018-08-11T12:03:48.000
dc.date.accessioned 2020-06-30T03:07:24Z
dc.date.available 2020-06-30T03:07:24Z
dc.date.copyright Fri Jan 01 00:00:00 UTC 2016
dc.date.embargo 2017-09-20
dc.date.issued 2016-01-01
dc.description.abstract <p>This thesis discloses catalytic, enantioselective dipolar cycloadditions to deliver new nitrogen-containing heterocycles and formal hydroarylations of olefins that have previously not been possible.</p> <p>Catalytic, enantioselective, dearomative cycloadditions of stabilized, α-substituted azomethine ylides with 3-nitroindoles occur in the presence of a catalytic complex generated from Cu(OTf)2 and (R)-Difluorphos. These reactions set four contiguous stereocenters, two of which are fully substituted. Overcoming the barrier of breaking aromaticity, this catalyst system delivers pyrrolo[3, 4b]indoles with exoà ´-selectivity in moderate-to-good yields (39-85%) with high diastereoselectivity (up to 98 : 1 : 1 dr) and enantioselectivity (up to 96% ee).</p> <p>Catalytic, enantioselective, dipolar cycloadditions of highly reactive nitrile imines with methyleneindolinones occur in the presence of a catalyst generated from Mg(NTf2)2 and a chiral aminoindanol-derived bisoxazoline ligand. The catalyst system designed overcomes a rapid competing background reaction to deliver spiro[pyrazolin-3,3′-oxindoles] in up to 98% yield and 99% ee.</p> <p>Conjugate additions of arylboronic acids to challenging 2-alkylchromones occur in aqueous medium in the presence of a catalyst system generated from Pd(TFA)2 and 1,10-phenanthroline. This system overcomes the problem of competing protodeboronation and biaryl-forming reactions to deliver 2-alkyl-2-aryl-chromanones in up to 90% yield, providing a new and effective means of generating a fully substituted carbon center.</p> <p>In all of these projects, effective catalyst design principles were established to overcome challenges that made these types of reactions previously impossible.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/etd/15918/
dc.identifier.articleid 6925
dc.identifier.contextkey 11169290
dc.identifier.doi https://doi.org/10.31274/etd-180810-5545
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath etd/15918
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/30101
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/etd/15918/Gerten_iastate_0097E_16059.pdf|||Fri Jan 14 20:48:40 UTC 2022
dc.subject.disciplines Chemistry
dc.subject.disciplines Organic Chemistry
dc.subject.keywords Catalyst
dc.subject.keywords Enantioselective
dc.subject.keywords Flavanone
dc.subject.keywords Lewis Acid
dc.subject.keywords Pyrroloindoline
dc.subject.keywords Spirooxindole
dc.title Catalytic methods for the synthesis of spirooxindoles, pyrroloindolines, and flavanones
dc.type article
dc.type.genre dissertation
dspace.entity.type Publication
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
thesis.degree.discipline Organic Chemistry
thesis.degree.level dissertation
thesis.degree.name Doctor of Philosophy
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