Investigations pertaining to the rhodium(I)-catalyzed addition of arylboronic acids to (arylsulfonyl)acetonitriles were undertaken. The resulting carbon-carbon bond forming reaction has led to the efficient synthesis of novel stereoselective (Z)-β-sulfonylvinylamines, which upon acidic hydrolysis, afford useful β-keto sulfones possessing a diverse range of aryl and sulfonyl substituents. The synthetic utility of these (Z)-β-sulfonylvinylamines was subsequently explored by generating the corresponding 1-aza-allyl anion equivalents under basic conditions. This interesting anionic intermediate was then introduced to various α,β-unsaturated systems to produce a diverse array of functionalized pyridine derivatives including unsymmetrical polysubstituted pyridines.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/31293 |
| Date | 13 December 2011 |
| Creators | Lau, Chan Tong |
| Contributors | Lautens, Mark |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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