The development of ligands for C-H functionalization utilizing amino acid derived directing groups
| dc.contributor.author | Stache, Erin Elizabeth, author | |
| dc.contributor.author | Ferreira, Eric M., advisor | |
| dc.contributor.author | Rovis, Tomislav, committee member | |
| dc.contributor.author | Inamine, Julia, committee member | |
| dc.date.accessioned | 2007-01-03T08:22:06Z | |
| dc.date.available | 2007-01-03T08:22:06Z | |
| dc.date.issued | 2011 | |
| dc.description.abstract | The functionalization of unreactive bonds has become a focus of new reaction methodology. The foremost difficulty lies within achieving high levels of chemo-, regio-, and stereoselectivity without the need for molecular complexity. The aim of my project was to develop a catalyst system that could direct a C-H functionalization by forming a transient covalent attachment to a simple substrate and release the substrate after the transformation. I have developed two asymmetric catalysts for the C-H acetoxylation of sp3 and sp2 bonds. The sp3 C-H acetoxylation occurs with high levels of diastereoselectivity, demonstrating the compatibility of this idea for enantioselective C-H functionalization. In the course of my asymmetric ligand development, I engineered a stereoretentive synthesis for the formation of quaternary asymmetric amino amides. The straightforward synthesis involves facile, high yielding conversion of L-proline into a broad scope of differentially substituted amides with excellent enantioselectivity. Furthermore, my exploration into amino acid derived ligands has uncovered a new method for C-C bond formation. The coupling of aryl substrates, originating from aryl sulfonamides, with olefins in a Heck-type transition metal catalyzed process has been discovered from examining serine scaffolds. This transformation may become a useful addition to the arsenal of C-C bond forming reactions. | |
| dc.format.medium | born digital | |
| dc.format.medium | masters theses | |
| dc.identifier | Stache_colostate_0053N_10817.pdf | |
| dc.identifier | ETDF2011400327CHEM | |
| dc.identifier.uri | http://hdl.handle.net/10217/70829 | |
| 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.title | The development of ligands for C-H functionalization utilizing amino acid derived directing groups | |
| 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.) |
Files
Original bundle
1 - 1 of 1
Loading...
- Name:
- Stache_colostate_0053N_10817.pdf
- Size:
- 6.65 MB
- Format:
- Adobe Portable Document Format
- Description: