Iridium-catalyzed C-C bond formation : development of crotylation and methallylation reactions through transfer hydrogenation

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dc.contributor.advisorKrische, Michael J.en
dc.contributor.committeeMemberAnslyn, Eric V.en
dc.creatorTownsend, Ian A.en
dc.date.accessioned2012-07-19T14:06:42Zen
dc.date.accessioned2017-05-11T22:26:06Z
dc.date.available2012-07-19T14:06:42Zen
dc.date.available2017-05-11T22:26:06Z
dc.date.issued2012-05en
dc.date.submittedMay 2012en
dc.date.updated2012-07-19T14:06:52Zen
dc.descriptiontexten
dc.description.abstractUnder the conditions of transfer hydrogenation utilizing chromatographically purified ortho-cyclometallated iridium C,O-benzoate precatalysts, enantioselective carbonyl crotylation and methallylation can be performed in the absence of stoichiometric metallic reagents and stoichiometric chiral modifiers. In the case of carbonyl crotylation, use of a preformed precatalyst rather than an in situ generated catalyst results in lower reaction temperatures, providing generally higher diastereoselectivity and yields. By utilizing a more reactive leaving group in chloride over acetate on our methallyl donor, the inherently shorter lifetime of the olefin π-complex is compensated for, giving our group’s first report of reactivity utilizing 1,1-disubstituted allyl donors.en
dc.description.departmentChemistryen
dc.format.mimetypeapplication/pdfen
dc.identifier.slug2152/ETD-UT-2012-05-5582en
dc.identifier.urihttp://hdl.handle.net/2152/ETD-UT-2012-05-5582en
dc.language.isoengen
dc.subjectTransfer hydrogenationen
dc.subjectC-C bond formationen
dc.subjectCatalysisen
dc.subjectIridiumen
dc.subjectCrotylationen
dc.subjectMethallylationen
dc.subjectPolyketideen
dc.subjectPolypropionateen
dc.titleIridium-catalyzed C-C bond formation : development of crotylation and methallylation reactions through transfer hydrogenationen
dc.type.genrethesisen

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