Metal-free functionalisation of alkenes

  • Carla Alamillo Ferrer

Student thesis: Doctoral Thesis

Abstract

This thesis describes two novel metal-free transformations, a method to selectively synthesise anti-diols from readily available alkene starting materials and an oxidative heterocyclisation of homoallylic nucleophiles for the synthesis of biologically significant hetereocycles.Chapter 1 describes a metal-free methodology for the preparation of anti-diols from alkenes. A selection of trans-stilbene and styrene derivatives were synthesised and reacted under optimal reaction conditions to give anti-diols in good to excellent yields and selectivities. Substituted indene and naphthalene starting materials were also prepared providing significantly better syn:anti diastereoselectivities.Chapter 2 demonstrates a novel oxidative heterocyclisation under metal-free conditions for the preparation of oxygenated heterocycles, a class of compounds with potential biological applications. For this reason, Citalopram, an antidepressant, was synthesised using this approach. This transformation provided access to γ-lactone, tetrahydrofuran and isobenzofuranone scaffolds in high levels of diastereoselectivity. Chapter 3 represents a new methodology for the intramolecular aminohydroxylation of alkenes from protected homoallylic amines in the presence of a malonoyl peroxide. This transformation was also applied to N-protected cinnamylhydroxylamines for the generation of isoxazolidines. Chapter 4 describes the experimental procedures and analytical data generated for all the compounds synthesised. Chapters 5 and 6 contain the appendix and bibliography sections of the thesis.
Date of Award1 Apr 2017
LanguageEnglish
Awarding Institution
  • University Of Strathclyde
SponsorsEPSRC (Engineering and Physical Sciences Research Council)
SupervisorNicholas Tomkinson (Supervisor) & (Supervisor)

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