This thesis contains the synthesis of a series of novelligands that include the
enantiomerically pure 2-oxazoline moiety. The thesis also considers the application of new
nucleophiles for the palladium catalysed allylic substitution reaction. The synthesis of
enantiomerically enriched analogues of y-amino butyric acid (GABA) is presented.
The first series of ligands are designed as analogues of acetyl acetonate (acac). The ligands
include the enantiomerically pure 2-oxazoline ring and a carbonyl moiety. The ligands are
available in good yield in two steps. The second series of ligands include a ligating sulfur
atom. The synthesis of novel oxazoline-sulfide ligands is detailed. The diastereoselective
oxidation of these ligands is considered. Diastereomerically pure oxazoline-sulfoxide ligands
are prepared in good yield.
New nucleophiles are applied to the palladium catalysed allylic substitution reaction. The
substitution products are available in good yield and with excellent stereoselectivity. The
synthesis of analogues of GABA is considered. The preparation of enantiomerically enriched
a-substituted-y-amino butyric acids is presented. The stereocentre is introduced in the first
step of the synthesis. The analogues are subsequently isolated in good yield after six steps.
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.