Catalytic asymmetric Stetter reaction: intramolecular desymmetrization of cyclohexadienone and intermolecular reaction of glyoxamide
| dc.contributor.author | Liu, Qin, author | |
| dc.contributor.author | Rovis, Tomislav, advisor | |
| dc.date.accessioned | 2024-03-13T20:12:23Z | |
| dc.date.available | 2024-03-13T20:12:23Z | |
| dc.date.issued | 2009 | |
| dc.description.abstract | A series of cyclohexadienones were synthesized through dearomatization of phenols. The asymmetric intramolecular desymmetrizations of these substrates via Stetter reactions afford hydrobenzofuranones in good yields and excellent selectivities. Up to three contiguous stereocenters, as well as quaternary stereocenter, have been generated. An asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates has been successfully developed. These reactions are catalyzed by a pyrrolidinone-derived carbene catalyst, and proceed in good yields with high asymmetric induction. When alkylidene ketoamides are employed, the reactions afford desired β-ketoamides in good yields, excellent enantioselectivities, and good diastereoselectivities. A carbene-catalyzed asymmetric redox reaction of ynal has been investigated. Cyclohexadienone-tethered ynal and alkylidenemalonate-tethered ynal were demonstrated as suitable substrates for the redox reaction. The desired products were obtained with moderate yields and modest selectivities. | |
| dc.format.medium | born digital | |
| dc.format.medium | doctoral dissertations | |
| dc.identifier | ETDF_Liu_2009_3374659.pdf | |
| dc.identifier.uri | https://hdl.handle.net/10217/237851 | |
| 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.rights.license | Per the terms of a contractual agreement, all use of this item is limited to the non-commercial use of Colorado State University and its authorized users. | |
| dc.subject | asymmetric Stetter reaction | |
| dc.subject | carbenes | |
| dc.subject | cyclohexadienone | |
| dc.subject | desymmetrization | |
| dc.subject | glyoxamide | |
| dc.subject | organic chemistry | |
| dc.title | Catalytic asymmetric Stetter reaction: intramolecular desymmetrization of cyclohexadienone and intermolecular reaction of glyoxamide | |
| 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 | Doctoral | |
| thesis.degree.name | Doctor of Philosophy (Ph.D.) |
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