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Exploring regiocontrolled gold-catalysed alkyne activation for efficient synthesis of nitogen heterocycles

Chatzopoulou, Elli (2015)
Ph.D. thesis, University of Birmingham.

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Abstract

In this thesis the development of regiocontrolled gold-catalysed reactions for the synthesis of complex heterocycles are described.

A new methodology for the formation of all-carbon fully substituted oxazoles was designed and developed, through a novel gold-catalysed intermolecular formal [3+2]-cycloaddition across the π-system of electron-rich internal alkynes by employing conjugated \(N\)-ylides as \(N\)-nucleophilic 1,3-\(N\),\(O\)-dipole equivalents. This intermolecular addition to unsymmetrical internal alkynes represents a considerable regioselectivity and reactivity challenge, as there are no examples of intermolecular atom-transfer nitrene addition.

A new design of substrates incorporating an electron-rich π-system and a tethered oxidant or a nitrene delivery system was investigated. Several strategies towards the formation of these systems were proposed and the exhibiting limitations were identified.

A novel gold-catalysed reaction has been developed for the formation of complex polycyclic systems, which involves a [1,5]-hydride transfer/cyclisation cascade of functionalised aromatic and aliphatic ynamides. Under mild conditions, the process rapidly generates three fused ring systems by the formation of three new C(sp\(^3\))-C(sp\(^3\)) bonds and up to four contiguous stereogenic centres, in a single manipulation.

Type of Work:Ph.D. thesis.
Supervisor(s):Davies, Paul
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Additional Information:

Embargo until: 31/12/2017

Subjects:QD Chemistry
Institution:University of Birmingham
ID Code:6110
This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder.
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