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.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:739239 |
| Date | January 2018 |
| Creators | Mostafa, Mohamed A. B. |
| Publisher | University of Glasgow |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://theses.gla.ac.uk/8779/ |
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