Telescoping of transition metal catalysed and biocatalysed reactions

Simple item page
dc.availability.bitstreamcontrolled
dc.check.infoControlled Access
dc.contributor.advisorMoynihan, Humphrey A.en
dc.contributor.authorKelly, Áine
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2021-05-27T10:25:03Z
dc.date.available2021-05-27T10:25:03Z
dc.date.issued2020-11-10
dc.date.submitted2020-11-10
dc.descriptionControlled Access
dc.description.abstractThis 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.description.statusNot peer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKelly, A. C. 2020. Telescoping of transition metal catalysed and biocatalysed reactions. PhD Thesis, University College Cork.en
dc.identifier.endpage378en
dc.identifier.urihttps://hdl.handle.net/10468/11398
dc.language.isoenen
dc.publisherUniversity College Corken
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.rights© 2020, Áine Kelly.en
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectChemistryen
dc.subjectBiocatalysisen
dc.subjectReaction telescopingen
dc.subjectOrganic chemistryen
dc.subjectSynthetic chemistryen
dc.subjectTransition metal catalysisen
dc.titleTelescoping of transition metal catalysed and biocatalysed reactionsen
dc.typeDoctoral thesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD - Doctor of Philosophyen
Files
Original bundle
Now showing 1 - 3 of 3
Thumbnail Image
Name:
Telescoping of Transition Metal Catalysed and Biocatalysed Reactions.docx
Size:
6.32 MB
Format:
Microsoft Word XML
Description:
Full Text E-thesis (Word)
Thumbnail Image
Name:
Telescoping of Transition Metal Catalysed and Biocatalysed Reactions.pdf
Size:
7.92 MB
Format:
Adobe Portable Document Format
Description:
E-thesis Pdf
Thumbnail Image
Name:
3. SubmissionforExaminationFormAineKelly - Aine Christine Kelly.pdf
Size:
384.95 KB
Format:
Adobe Portable Document Format
Description:
Submission for Examination Form
License bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
license.txt
Size:
5.2 KB
Format:
Item-specific license agreed upon to submission
Description:
Download
Collections
Research Theses
Analytical & Biological Chemistry Research Facility - Doctoral Theses
Chemistry - Doctoral Theses
College of Science, Engineering and Food Science - Doctoral Theses
Synthesis and Solid State Pharmaceutical Centre (SSPC) - Doctoral Theses