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dc.contributor.advisorLam, Hon
dc.contributor.advisorHulme, Alison
dc.contributor.advisorLeigh, David
dc.contributor.authorKujawa, Szymon
dc.date.accessioned2015-11-11T14:21:03Z
dc.date.available2015-11-11T14:21:03Z
dc.date.issued2015-11-26
dc.identifier.urihttp://hdl.handle.net/1842/11697
dc.description.abstract1. Enantioselective Pd(II)-Catalysed Nucleophilic Additions of 2- Alkylazaarenes The first project deals with enantio- and diastereoselective palladium(II)-catalysed nucleophilic additions of 2-alkylazaarenes to N-Boc imines and nitroalkenes. Under the optimised reaction conditions high levels of diastereo- and enantioselection of the addition products were achieved. Introduction of the electron-withdrawing group at the aryl ring of the substrate allows running the reaction under mild, experimentally convenient reaction conditions. The new described method allows the enantioselective synthesis of 2-(β-aminoalkyl)azaarenes, which are substructures found in drug candidates molecules for the treatment of type 2 diabetes and schizophrenia. 2. Synthesis of Spirocyclic Enones via Rh(III)-Catalysed C–H Functionalisation The second project describes the synthesis of spirocyclic enones by rhodium(III)- catalysed dearomatising oxidative annulation of 2-alkenylphenols with alkynes and 1,3-enynes. A good to high yield with great regioselectivity was obtained. The further synthetic utility of the product was also investigated and led to the formation of highly functionalised tetracycles via 1,6 conjugation addition reaction.en
dc.contributor.sponsorEngineering and Physical Sciences Research Council (EPSRC)en
dc.language.isoenen
dc.publisherThe University of Edinburghen
dc.relation.hasversionDiastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes, Best, D.; Kujawa, S.; Lam, H. W. J. Am. Chem. Soc. 2012, 134, 18193-18196en
dc.relation.hasversionSynthesis of Spirocyclic Enones by Rhodium-Catalyzed Dearomatizing Oxidative Annulation of 2-Alkenylphenols with Alkynes and Enynes, Kujawa, S.; Best, D.; Burns, D. J.; Lam, H. W. Chem. Eur. J. 2014, 20, 8599-8602en
dc.subjectenantioselective synthesisen
dc.subject2-(β-aminoalkyl)azaarenesen
dc.subjectspirocyclic enonesen
dc.subjectsynthesisen
dc.titleRapid generation of molecular complexity under Pd(II) and Rh(III) catalysisen
dc.typeThesis or Dissertationen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD Doctor of Philosophyen


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