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Title: Copper-catalysed cross-couplings : applications in target synthesis and multicomponent reactions
Author: Ruscoe, Rebecca
ISNI:       0000 0005 0289 2900
Awarding Body: University of Manchester
Current Institution: University of Manchester
Date of Award: 2017
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Copper-catalysed reactions have proved to be extremely valuable, especially for the formation of C-C bonds in organic chemistry. This has been enhanced by the recent advances in methods that replace less abundant, toxic metals with copper for the efficient construction of useful building blocks for synthesis. Here we present the use of copper catalysis in two very different projects. The first utilises copper in a 1,4-conjugate addition to a chloroenone, to form an all carbon quaternary centre. This allows access to cascade cyclisation substrates that on exposure to samarium diiodide result in an efficient cascade reaction to form the tricyclic core of pleuromutilin analogues. The second project details the development of an enantioselective three-component coupling reaction between allenes, diboranes, and imines catalysed by copper. This procedure assembles homoallylic amines with adjacent stereocentres with high enantiocontrol, and exploits a commercially available chiral ligand. The approach has been extended to electrophiles other than imines, with preliminary work on an enantioselective borylcyanation of allenes being reported.
Supervisor: Flitsch, Sabine ; Procter, David Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Cyanation ; Antibacterials ; Borylation ; Allenes ; Samarium ; Pleuromutilin ; Conjugate addition ; Copper-catalysis ; Imines