Montmorillonite-catalyzed allylation of aldehydes with potassium allyltrifluoroborate is a convenient method for the synthesis of homoallylic alcohols. This chemistry was applied to various unsaturated aldehydes, and the homoallylic alcohols produced were used as common intermediates for two separate but related synthetic routes to α,β-unsaturated ketones. In the first route, oxidation of the alcohol to the ketone was followed by base-catalyzed isomerization of the olefin to the α,β-unsaturated ketone. This was subjected to ring closing metathesis conditions to afford the cyclic enone of ring size n. In the other route, ring-closing metathesis was performed first, followed by oxidation of the alcohol and isomerization of the olefin to the cyclic enone of ring size n+1.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/29573 |
| Date | 25 August 2011 |
| Creators | Kafal, Adam |
| Contributors | Batey, Robert A. |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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