Telescoping of transition metal catalysed and biocatalysed reactions

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dc.contributor.advisor Moynihan, Humphrey A. en Kelly, Áine 2021-05-27T10:25:03Z 2021-05-27T10:25:03Z 2020-11-10 2020-11-10
dc.identifier.citation Kelly, A. C. 2020. Telescoping of transition metal catalysed and biocatalysed reactions. PhD Thesis, University College Cork. en
dc.identifier.endpage 378 en
dc.description.abstract This thesis describes the telescoping reactions which exploit the diverse catalytic approaches of transition metal catalysis and biocatalysed processes. These processes would normally have conditions that are incompatible. Telescoping these processes into a single process will provide powerful enantioselectivity which exploits the efficiency of transition metal catalysis and the stereoselectivity of biocatalysis. Chapter one provides an overview of asymmetric synthesis, both –diazocarbonyl compound synthesis and reactions, and biotransformations. It also gives an overview of telescoping systems from the literature. The results of this research are discussed in both chapter two and three. Chapter two describes the initial work undertaken during this project including attempting intramolecular X–H insertion reactions and intramolecular C–H insertion and then the Baker’s yeast reduction of those products. The batchwise step–by–step transformations were undertaken initially and then telescoped together overcoming problems associated with the process. Chapter three describes the C–H intramolecular reactions with both rhodium (II) acetate and copper (II) triflate to produce a range of 2–benzenesulfonyl substituted cyclopentanone compounds. These compounds were then kinetically resolved via a Baker’s yeast mediated reduction. These individual steps were optimised before they were telescoped together. The range of 2–benzenesulfonyl substituted cyclopentanone compounds also underwent ring cleavage to give simple carboxylic acids which could then be desulfonylated to simple alcohol compounds with a stereocentre in the middle of the chain. Chapter four contains the full experimental details and spectral characterisation of all the compounds synthesised in this project, while the details of the chiral stationary phase HPLC analysis is included in the appendix. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher University College Cork en
dc.rights © 2020, Áine Kelly. en
dc.rights.uri en
dc.subject Chemistry en
dc.subject Biocatalysis en
dc.subject Reaction telescoping en
dc.subject Organic chemistry en
dc.subject Synthetic chemistry en
dc.subject Transition metal catalysis en
dc.title Telescoping of transition metal catalysed and biocatalysed reactions en
dc.type Doctoral thesis en
dc.type.qualificationlevel Doctoral en
dc.type.qualificationname PhD - Doctor of Philosophy en
dc.internal.availability Full text not available en
dc.description.version Accepted Version en
dc.contributor.funder Science Foundation Ireland en
dc.description.status Not peer reviewed en Chemistry en
dc.internal.conferring Summer 2021 en
dc.internal.ricu Analytical and Biological Chemistry Research Facility en
dc.internal.ricu Synthesis and Solid State Pharmaceutical Centre (SSPC) en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ en
dc.availability.bitstream controlled 2023-05-30

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© 2020, Áine Kelly. Except where otherwise noted, this item's license is described as © 2020, Áine Kelly.
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