Thesis-2002-Reignier.pdf (3.46 MB)
Sulfur in asymmetric synthesis
thesis
posted on 2018-07-04, 13:36 authored by Serge ReignierThis thesis is divided into three chapters. The first chapter is a review of the literature methods
utilised to date in the synthesis of non-racemic chiral sulfoxides, including resolution,
stereospecific nucleophilic substitution at sulfur, asymmetric oxidation and enzymatic methods
Also, this first chapter introduces briefly the palladium-catalysed allylic nucleophilic substitution
reaction. It covers the nature of different factors which can influence on the enantiomeric excess.
The second section deals with our approaches to the synthesis of potentially chelating sulfoxides
of high enantiomeric purity and their subsequent application, mainly in the process of palladium-catalysed
allylic nucleophilic substitution reactions as chiral ligands, but also their application as
chiral auxiliaries in the synthesis of chiral α-hydroxy or α-amino ketones. This second chapter
also deals with the design of a new class of chiral ammo-sulfides as ligand in the palladium-catalysed
allylic nucleophilic substitution reaction.
The most successful ligand synthesised enantiomerically pure N-(1,1-dimethylethyl)-N-(1S,2S)-2-[(1,1-dimethylethyl)thio]-1-methyl-2-phenylethyl-N-methylamine was applied successfully to
the palladium-catalysed allylic nucleophilic substitution reaction, furnishing the product in up to
89% ee.
The third part of this thesis deals with the experimental procedures undertaken in this work.
Funding
Loughborough University.
History
School
- Science
Department
- Chemistry
Publisher
© Serge ReignierPublisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2002Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en