Use this URL to cite or link to this record in EThOS:
Title: Solid-phase approaches to heterocycles using a sulfur linker cleaved by reduction with samarium (II) iodide
Author: Turner, Kristy L.
ISNI:       0000 0001 3539 0262
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2006
Availability of Full Text:
Access from EThOS:
Access from Institution:
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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available