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Title: Asymmetric synthesis of heterocycles via cation-directed cyclizations and rearrangements
Author: Lamb, Alan David
ISNI:       0000 0004 5356 909X
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2014
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The aim of this project was to utilize chiral cation-directed catalysis in the asymmetric synthesis of novel hererocycles. This goal was initially realized by the synthesis of azaindolines in high yields and enantioselectivities (Chapter 2). Extension of this methodology to substrates bearing two stereogenic centres was successful, although control over both diastereoselectivity and enantioselectivity in this process was modest. Finally the synthesis of heterocycles utilizing cation-directed rearrangement processes was examined, with proof of concept obtained for a novel asymmetric cyclization to form xanthenes.
Supervisor: Smith, Martin D. Sponsor: Engineering and Physical Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Synthetic organic chemistry ; Asymmetric catalysis ; phase-transfer catalysis ; methodology