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Title: Chiral cation-directed asymmetric 5-endo-trig cyclizations
Author: Johnston, Craig Paterson
ISNI:       0000 0004 2747 090X
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2013
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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.
Supervisor: Smith, Martin D. Sponsor: EPSRC ; Pfizer
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Physical Sciences ; Chemistry & allied sciences ; Asymmetric catalysis ; Catalysis ; Organic chemistry ; Organic synthesis ; Synthetic organic chemistry ; Baldwin's rules ; indanes ; phase-transfer catalysis ; asymmetric ; cyclization