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Title: A novel desymmetrisation approach towards chiral molecules, using 'click' chemistry
Author: Sheldon, Alexander
ISNI:       0000 0004 5916 1028
Awarding Body: University of East Anglia
Current Institution: University of East Anglia
Date of Award: 2016
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Typically, the popular click reaction between an alkyne and an azide forms a triazole in very high yield, but since this process does not produce a stereogenic centre, its use with chiral ligands has not been thoroughly investigated. Choosing a prochiral diyne as the starting material allows the click process to perform a desymmetrisation step. Desymmetrisation of prochiral molecules using click chemistry is a method that has had little attention in the past. Herein is described progress into a novel synthetic route to chiral molecules using this process. The first part of this thesis introduces the concept of chirality, why it is important, and how molecules with chirality are synthesised. Then, the importance of the click reaction and similar reactions are discussed. The second part of this thesis reports on the formation and characterisation of the bis-alkyne precursors, which are used in the key click chemistry step. Next, several azide compounds are discussed, as these are also required for the key step. The third part of this thesis is concerned with the main click chemistry step. There are sub-sections for the original racemic trial reactions, as well as a series of reactions assessing various ligands, culminating in a tuning of conditions for the best ligand. A general reaction scheme for the project is given below. Next follows the fourth part, which consists of some reactions performed in conjunction with a visiting project student. Whilst these are not key to my research, they are related to the main aim of a chiral click reaction. The final part of this thesis is the experimental section and the appendix.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available