Development of an asymmetric intermolecular stetter reaction and organocatalyst design
| dc.contributor.author | Glover, Garrett S., author | |
| dc.contributor.author | Rovis, Tomislav, advisor | |
| dc.contributor.author | Wood, John L., committee member | |
| dc.contributor.author | Kanatous, Shane, committee member | |
| dc.date.accessioned | 2007-01-03T05:56:29Z | |
| dc.date.available | 2007-01-03T05:56:29Z | |
| dc.date.issued | 2012 | |
| dc.description | Zip file contains the source code. | |
| dc.description.abstract | The intermolecular Stetter represents a powerful carbon-carbon bond forming reaction that involves addition of an acyl anion equivalent to an untethered Michael acceptor. Despite the appeal of rendering the intermolecular reaction asymmetric, this area remains particularly underdeveloped. We describe a catalytic asymmetric intermolecular Stetter reaction for the coupling of 2-pyridinecarboxaldehydes and β-substituted vinyl triflones. In pursuit of increasing the efficiency of this reaction, we developed a series of base-activated NHC pre-catalysts that are capable of catalyzing the intramolecular Stetter reaction without an external base. As an indirect result of our attempts to form activated pre-catalysts, we discovered a catalyst hydration product, that itself generates free-carbene in solution. Additionally, we gathered conclusive evidence for a previously unknown SNAR type decomposition pathway of an electron deficient triazolinylidene catalyst. | |
| dc.format.medium | born digital | |
| dc.format.medium | masters theses | |
| dc.format.medium | ZIP | |
| dc.format.medium | CIF | |
| dc.identifier | Glover_colostate_0053N_11012.pdf | |
| dc.identifier | Glover_colostate_0053N_11012_suppl.zip | |
| dc.identifier.uri | http://hdl.handle.net/10217/88358 | |
| dc.language | English | |
| dc.language.iso | eng | |
| dc.publisher | Colorado State University. Libraries | |
| dc.relation.ispartof | 2000-2019 | |
| dc.rights | Copyright 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.subject | asymmetric catalysis | |
| dc.subject | Stetter reaction | |
| dc.subject | organocatalysis | |
| dc.subject | NHC | |
| dc.subject | intermolecular | |
| dc.title | Development of an asymmetric intermolecular stetter reaction and organocatalyst design | |
| dc.type | Text | |
| dcterms.rights.dpla | This 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.discipline | Chemistry | |
| thesis.degree.grantor | Colorado State University | |
| thesis.degree.level | Masters | |
| thesis.degree.name | Master of Science (M.S.) |