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Synthesis and application of stereogenic nitrogen-containing ammonium salts as phase-transfer catalysts

Dutton, Mark Jason (2016)
Ph.D. thesis, University of Birmingham.

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Abstract

The chirality of nitrogen was at the forefront of chemistry over 110 years ago. Since then it has been widely under-acknowledged as a potential chirality source in organic synthesis. This thesis demonstrates the diastereoselective formation of stereogenic nitrogen-containing ammonium salts. Over 150 compounds were synthesised and employed as phase-transfer catalysts in order to assess the chiral-at-nitrogen influence on the outcome of two common phase-transfer-catalysed reactions. Several X-ray crystal structures of single diastereoisomer chiral-at-nitrogen ammonium salts were isolated as well as the synthesis of a library of secondary and tertiary amines.

Type of Work:Ph.D. thesis.
Supervisor(s):Fossey , J.S. and Preece, Jon Andrew
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Subjects:Q Science (General)
QD Chemistry
Institution:University of Birmingham
ID Code:6755
This unpublished thesis/dissertation is copyright of the author and/or third parties.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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