This thesis has focussed on <sup>18</sup>F-fluorination reactions activated by an organomediator, with the aim of broadening the scope of metal-free reactions in <sup>18</sup>F-radiosynthesis. <b>Chapter 1</b> provides an introduction to positron emission tomography (PET) and <sup>18</sup>Fradiochemistry, including radioisotope production and modes of activation in <sup>18</sup>Fradiosynthesis. In <b>Chapter 2</b>, the concept of chirality and its relevance in the context of radiotracer design is introduced. The previously disconnected fields of organomediated asymmetric fluorination and <sup>18</sup>F-radiosynthesis are merged for the first time via investigation of three distinct activation modes: chiral non-racemic secondary amine-mediated asymmetric α-<sup>18</sup>F-fluorination of aldehydes employing [<sup>18</sup>F]N-fluorobenzenesulfonimide; use of a phase transfer reagent for asymmetric <sup>18</sup>F-fluorocyclisation and application of a chiral nonracemic <sup>18</sup>F-fluorinating agent, chiral [<sup>18</sup>F]Selectfluor bis-triflate. Application of the first of these approaches to the radiosynthesis of the PET tracer (2S,4S)-4-[<sup>18</sup>F]fluoroglutamic acid with high d.r. is described. <b>Chapter 3</b> explores the use of hypervalent iodine reagents to mediate the oxidative fluorination of N-arylsulfonamides with nucleophilic fluoride via an umpolung approach. Preliminary studies on translation to radiosynthesis with [<sup>18</sup>F]fluoride are also disclosed. In <b>Chapter 4</b>, experimental data is provided for all compounds, as well as analytical and chiral HPLC traces for <sup>18</sup>F-reactions.
Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:730496 |
Date | January 2015 |
Creators | Buckingham, Faye |
Contributors | Gouverneur, Véronique |
Publisher | University of Oxford |
Source Sets | Ethos UK |
Detected Language | English |
Type | Electronic Thesis or Dissertation |
Source | https://ora.ox.ac.uk/objects/uuid:00774f21-9abf-4a4a-b4d3-1300e3ae3fa1 |
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