RECENT ADVANCES IN IMINIUM SALT CATALYSED ASYMMETRIC EPOXIDATION

Day, David (2013) RECENT ADVANCES IN IMINIUM SALT CATALYSED ASYMMETRIC EPOXIDATION. Doctoral thesis, University of East Anglia.

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Abstract

The research in this thesis depicts some of the most current developments in the area of
asymmetric epoxidation of alkenes using chiral iminium salt catalysts. The first chapter
reviews past and present developments in; catalytic asymmetric epoxidation, and covers the
application of this reaction towards the kinetic resolution of racemic olefins.
Chapter two is separated into two key areas; (i) asymmetric epoxidation as a tool in the kinetic
resolution of racemic chromene substrates, and (ii) investigations into the asymmetric
epoxidation of new N-protected dihydroquinoline substrates. In the first part of chapter two,
the first examples of kinetic resolution in epoxidation reactions using iminium salt catalysts
are reported, providing up to 98% ee in the epoxidation of racemic cis-chromenes.
The second part of chapter two details the first known examples of asymmetric epoxidation
upon nitrogen-protected dihydroquinoline substrates, affording enantioselectivities as high as
73% ee.
In both parts of chapter two, non-aqueous epoxidation conditions were employed using Page’s
dihydroisoquinolinium iminium salt catalyst. The later part of chapter two introduces a
biphenylazepinium iminium salt catalyst used under aqueous epoxidation conditions.
Chapter three includes experimental data for all the compounds mentioned in chapter two,
with chapter four containing HPLC traces to show determination of enantiomeric excess of
epoxides, and enantioenriched alkene traces.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Mia Reeves
Date Deposited: 11 Mar 2014 16:51
Last Modified: 11 Mar 2014 16:51
URI: https://ueaeprints.uea.ac.uk/id/eprint/48092
DOI:

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