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Dearomatising Addition of Tethered Organolithiums to Activated Benzene Derivatives
[Thesis]. Manchester, UK: The University of Manchester; 2011.
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Abstract
This thesis describes research carried out on the synthesis of lithiation precursors used to investigate the ability of oxazoline activated benzene derivatives to undergo dearomatising cyclisations.Chapter 1 illustrates previous work in the area of dearomatising additions, including intra- and inter-molecular dearomatisations. An overview of relevant work conducted within the Clayden group is also described.Chapter 2 narrates the synthesis of lithiation precursors that contain a (4R,5R)-4,5-diphenyloxazoline activating group on the aromatic ring. The attempts to lithiate and dearomatise these compounds are shown.Chapter 3 describes the synthesis of achiral oxazoline activated O-allylic pre-lithiation substrates, and their ability to undergo dearomatising cyclisations. Also described is the attempts to find a suitable protecting group for N-allylic dearomatising cyclisations.Chapter 4 outlines the investigations carried out for the stereoselective synthesis of (4R,5R)-4,5-diphenyloxazolines, which have been used for the activation towards dearomatising cyclisation.Chapter 5 is an overview of the thesis and outlines possible future work.Chapter 6 contains the experimental methods and data pertaining to Chapters 2 to 5.