Mostafa, Mohamed A.B.
(2018)
One-pot transition metal-catalysed processes for the synthesis of biologically active compounds.
PhD thesis, University of Glasgow.
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Abstract
The first section of this thesis describes the development of a one-pot Pd(II)-
catalysed Overman rearrangement, Ru(II)-catalysed ring closing enyne metathesis
reaction and a hydrogen bond-directed Diels-Alder reaction for the
diastereoselective synthesis of C-5 substituted aminobicyclo[4.3.0]nonanes in
good yields. To explore the late stage diversification of these compounds, further
work investigated a one-pot synthesis of a benzyldimethylsilyl-derived analogue.
The synthetic utility of this compound was demonstrated using C–C bond coupling
reactions, for the late stage synthesis of a range of sp3-rich bicyclononane
scaffolds with up to six stereogenic centres.
The second section of this thesis describes the development of a one-pot two-step
procedure for aryl C–H amination using iron and copper catalysis. Firstly, a mild
and highly regioselective method for the bromination (and chlorination) of arenes
via iron(III) triflimide activation of N-bromosuccinimide (or N-chlorosuccinimide)
was developed. The scope of both processes was explored for the synthesis of a
wide range of aromatic compounds and natural products. The one-pot iron(III)-
catalysed bromination/Cu(I)-catalysed N-arylation was then studied. After
optimisation, the one-pot two-step process allowed the synthesis of a large library
of para-aminated aryl compounds in high yields as single regioisomers.
Item Type: |
Thesis
(PhD)
|
Qualification Level: |
Doctoral |
Keywords: |
Metal catalysis, one-pot process, Overman rearrangement, ring closing enyne metathesis,
halogenation, ionic liquid, N-arylation, C-N coupling, Ullman-type coupling, ionic liquid. |
Subjects: |
Q Science > QD Chemistry |
Colleges/Schools: |
College of Science and Engineering > School of Chemistry |
Supervisor's Name: |
Sutherland, Dr. Andrew |
Date of Award: |
2018 |
Depositing User: |
mr Mohamed Mostafa
|
Unique ID: |
glathesis:2018-8779 |
Copyright: |
Copyright of this thesis is held by the author. |
Date Deposited: |
19 Feb 2018 09:37 |
Last Modified: |
26 Mar 2018 08:17 |
URI: |
http://theses.gla.ac.uk/id/eprint/8779 |
Related URLs: |
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