Solid-phase approaches to heterocycles using a sulfur linker cleaved by reduction with samarium (II) iodide

Turner, Kristy L (2006) Solid-phase approaches to heterocycles using a sulfur linker cleaved by reduction with samarium (II) iodide. PhD thesis, University of Glasgow.

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Abstract

Linker strategies lie at the heart of solid phase and combinatorial chemistry. HASC (alpha-Hetero-Atom Substituted Carbonyl) linkers have recently been developed and can be cleaved in a traceless manner using SmI[2]. My project was concerned with assessing the compatibility of HASC linkers with palladium-catalysed transformations. More specifically, we wished to use the linker system in conjunction with palladium chemistry in the solid-phase synthesis of important heterocyclic systems. We began by examining palladium-catalysed alpha-arylations as the basis of a possible solid-phase route to oxindoles and alpha-aryl carboxylic acids. The second part of my project involved the development of a solid-phase route to tetrahydroquinolones using a microwave-assisted Heck reaction and Michael cyclisation as the key steps. During this work, we also showed the feasibility of a cyclative-cleavage strategy using the HASC linker, where cleavage of the link with SmI2] is followed by cyclisation to give a heterocyclic product directly.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Additional Information: Adviser: David Procter
Keywords: Inorganic chemistry.
Colleges/Schools: College of Science and Engineering > School of Chemistry
Date of Award: 2006
Depositing User: Enlighten Team
Unique ID: glathesis:2006-74078
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 07 Aug 2019 10:56
Last Modified: 07 Aug 2019 11:00
URI: http://theses.gla.ac.uk/id/eprint/74078
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