Cascading cycloadditions for polycyclic sp\(^3\) -rich architecture

Ball-Jones, Matthew Phillip (2017). Cascading cycloadditions for polycyclic sp\(^3\) -rich architecture. University of Birmingham. Ph.D.

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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.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: None/not applicable
Subjects: Q Science > QD Chemistry


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