Use this URL to cite or link to this record in EThOS: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.739239
Title: One-pot transition metal-catalysed processes for the synthesis of biologically active compounds
Author: Mostafa, Mohamed A. B.
ISNI:       0000 0004 7226 4988
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2018
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.739239  DOI: Not available
Keywords: QD Chemistry
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