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Title: Rapid generation of molecular complexity under Pd(II) and Rh(III) catalysis
Author: Kujawa, Szymon
ISNI:       0000 0004 5368 8275
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2015
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1. 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.
Supervisor: Lam, Hon; Hulme, Alison; Leigh, David Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: enantioselective synthesis ; 2-(ß-aminoalkyl)azaarenes ; spirocyclic enones ; synthesis