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Title: Chiral counter-ion controlled asymmetric electrocyclic reactions
Author: Knipe, Peter Clarke
ISNI:       0000 0004 2744 5309
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2012
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The aim of this project was to develop new catalytic methods to control asymmetry in electrocyclic reactions, and to apply these methods to generate complex molecules. Initial efforts were directed towards the catalysis of anionic 8π electrocyclizations (Chapter 2 and Figure i). 8π electrocyclization was not achieved due to issues with alkene geometry and anion stability. Our efforts were then directed towards using phase-transfer catalysis to generate complex polycyclic compounds via a cascade electrocyclization-1,4-addition (Chapter 3 and Figure ii). Pyrrolidines and indolizidines were generated in excellent yield from simple starting-materials with high levels of stereocontrol. Finally, we investigated the catalysis of a 6π [1,6] electrocyclization to generate dihydroquinolones (Chapter 4 and Figure iii). A novel BINOL-derived copper(II) catalyst was developed, and afforded dihydroquinolones directly from their amine and aldehyde precursors with good yields and enantioselectivities.
Supervisor: Smith, Martin D.; Brennan, Paul E. Sponsor: EPSRC ; Pfizer
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemistry & allied sciences ; Asymmetric catalysis ; Catalysis ; Heterocyclic chemistry ; Organic chemistry ; Organic synthesis ; Synthetic organic chemistry ; Electrocyclization ; asymmetric ; organic