One-pot transition metal-catalysed processes for the synthesis of biologically active compounds

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
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