Due to the scarcity of energy resources that we are facing today, there is an increasing need for new methodology developments that are green and sustainable while minimizing unnecessary substrate pre-functionalization, by-product formation and waste generation. In this context, asymmetric rhodium-catalyzed hydroacylation is an atom-economical method for the preparation of chiral ketone derivatives from aldehyde and olefin precursors. This transformation is also applicable to keto-aldehyde precursors en route to chiral lactones. This dissertation describes the development of three specific methodologies, namely: 1) the synthesis of enantioenriched cyclopropyl ketones by enantio- and diastereoselective intermolecular rhodium-catalyzed hydroacylation of cyclopropenes, 2) the synthesis of enantioenriched phthalides by enantioselective rhodium-catalyzed intramolecular hydroacylation of ketones, and 3) the synthesis of tertiary branched allylic amines by silver-catalyzed ring-opening hydroamination of cyclopropenes.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OTU.1807/32865 |
| Date | 31 August 2012 |
| Creators | Phan, Diem |
| Contributors | Dong, Vy Maria |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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