| 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 |
