Catalytic enantioselective conjugate addition of metalated heteroaryl nucleophiles

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Catalytic enantioselective conjugate addition of metalated heteroaryl nucleophiles

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dc.contributor.advisor Martin, Stephen F.
dc.creator Abbott, Lily Katherine
dc.date.accessioned 2010-11-05T15:57:28Z
dc.date.accessioned 2010-11-05T15:57:37Z
dc.date.available 2010-11-05T15:57:28Z
dc.date.available 2010-11-05T15:57:37Z
dc.date.created 2010-05
dc.date.issued 2010-11-05
dc.date.submitted May 2010
dc.identifier.uri http://hdl.handle.net/2152/ETD-UT-2010-05-1466
dc.description.abstract This report details the discovery of a method for rhodium catalyzed asymmetric conjugate additions of heteroaryl nucleophiles to α,β-unsaturated carbonyl compounds. This work has successfully employed heteraryl titanates in enantioselective conjugate addition to α,β-unsaturated carbonyl compounds for the first time. Moreover, the utility of benzofuranyl, benzothiophenyl, and pyrrolo zinc reagents has been exemplified in enantioselective conjugate additions. We have found that the precatalyst [Rh(COD)acac]/OMeBIPHEP is broadly effective for enantioselective conjugate additions. Each heterocycle tested exhibited unique reactivity with respect to both conversion and enantioselectivity; reactivities of heteroaryl zinc reagents and heteroaryl titanates in enantioselective conjugate additions to α,β-unsaturated carbonyl compounds are sometimes complementary. Efforts directed towards the development of a method for rhodium-free enantioselective conjugate addition of furan to α,β-unsaturated carbonyl compounds are also described.
dc.format.mimetype application/pdf
dc.language.iso eng
dc.subject Enantioselective conjugate addition
dc.subject Heteroaryl zinc reagent
dc.subject Titanate
dc.subject Rhodium catalysis
dc.title Catalytic enantioselective conjugate addition of metalated heteroaryl nucleophiles
dc.date.updated 2010-11-05T15:57:38Z
dc.contributor.committeeMember Siegel, Dionicio R.
dc.description.department Chemistry and Biochemistry
dc.type.genre thesis
dc.type.material text
thesis.degree.department Chemistry and Biochemistry
thesis.degree.discipline Chemistry
thesis.degree.grantor University of Texas at Austin
thesis.degree.level Masters
thesis.degree.name Master of Arts

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