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Title: Dearomatising addition of tethered organolithiums to activated benzene derivatives
Author: Harvey, Rebecca
ISNI:       0000 0004 2708 2261
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2011
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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.
Supervisor: Clayden, Jonathan Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available