Thesis
Metal-free functionalisation of alkenes
- Creator
- Rights statement
- Awarding institution
- University of Strathclyde
- Date of award
- 2017
- Thesis identifier
- T14684
- Person Identifier (Local)
- 201384145
- Qualification Level
- Qualification Name
- Department, School or Faculty
- 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.
- Resource Type
- DOI
- Date Created
- 2017
- Former identifier
- 9912563992902996
- Embargo Note
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