A novel desymmetrisation approach towards chiral molecules, using "click" chemistry

Sheldon, Alexander (2016) A novel desymmetrisation approach towards chiral molecules, using "click" chemistry. Doctoral thesis, University of East Anglia.

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Abstract

Typical ly, the popular cl ick react ion between an alkyne and an azide forms
a t riazole in very high yield, but since this process does not produce a
stereogenic cent re, i t s use wi th chi ral l igands has not been thoroughly
invest igated. Choosing a prochi ral diyne as the start ing mater ial al lows
the cl ick process to perform a desymmet risat ion step. Desymmet risat ion
of prochi ral molecules using cl ick chemist ry is a method that has ha d l i t t le
at tent ion in the past . Herein is descr ibed progress into a novel synthet ic
route to chi ral molecules using this process.
The f i rst part of this thesis int roduces the concept of chiral i ty, why i t is
important , and how molecules wi th chi ral i ty are synthesised. Then, the
importance of the cl ick react ion and simi lar react ions are discussed.
The second part of this thesis repor ts on the format ion and
characterisat ion of the bis-alkyne precursors, which are used in the key
cl ick chemist ry step. Next , several azide compounds are discussed, as
these are also requi red for the key step.
The third part of this thesis is concerned wi th the main cl ick chemist ry
step. There are sub-sect ions for the original racemic t rial react ions, as
wel l as a series of react ions assessing var ious l igands, culminat ing in a
tuning of condi t ions for the best l igand. A general react ion scheme for
the project is given below.
Next fol lows the fourth part , which consists of some react ions performed
in conjunct ion wi th a visi t ing project student . Wh i lst these are not key to
my research, they are related to the main aim of a chiral cl ick react ion.
The f inal part of this thesis is the experimental sect ion and the appendix.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Stacey Armes
Date Deposited: 28 Jun 2016 15:47
Last Modified: 28 Jun 2016 15:47
URI: https://ueaeprints.uea.ac.uk/id/eprint/59616
DOI:

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