The primary objective of this research project was to develop a novel protocol for the synthesis of densely functionalized optically enriched indanes through a chiral cation directed 5-endo-trig ring closure. In chapter two, a convergent strategy for the construction of the cyclization precursors is reported, which employs two easily adapted fragments. In chapter three, a range of quaternary ammonium salts are screened to establish the optimal phase-transfer conditions for this system. A variety of substrates were evaluated to probe the scope and limitations of this methodology. Finally, two potential mechanistic pathways for this enigmatic process are outlined and discussed in chapter four.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:581346 |
| Date | January 2013 |
| Creators | Johnston, Craig Paterson |
| Contributors | Smith, Martin D. |
| Publisher | University of Oxford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://ora.ox.ac.uk/objects/uuid:a21b6cb4-1b1b-48ab-9fc2-252916992598 |
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