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Title: Cascading cycloadditions for polycyclic sp³-rich architecture
Author: Ball-Jones, Matthew Phillip
ISNI:       0000 0004 7432 2926
Awarding Body: University of Birmingham
Current Institution: University of Birmingham
Date of Award: 2017
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This thesis describes the formation of complex 3-dimensional polycyclic heterocycles via intramolecular Diels-Alder reactions of highly functionalised 4-aminooxazoles. The research presented discusses the advances made in the formation of alkene and alkyne tethered aminides alongside the synthesis of a range of 1,6- and 1,7- enynamides and the rapid transformation of such components into a densely functionalised core. The scope of this process, using both C-2 and C-5 dienophile-tethered oxazoles is discussed and the potential of 1,6-enynamides to undergo cycloisomerisation under gold-catalysis is unveiled. Mechanisms for both the cycloisomerisation and the oxazole formation are provided, with brief investigations into inner and outer sphere processes. The gold-catalysed formal (3+2)-dipolar cycloaddition of both aminides and dioxazoles with thioalkynes is also presented, with the production of a range of diversely functionalised 5-thiooxazoles. Preliminary investigations into the use of Bronsted acid catalysis for the synthesis of 4-thiooxazoles is discussed alongside mechanistic proposals.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry