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Title: C-H functionalisation of 2-aryl cyclic 1,3-dicarbonyl compounds ; Enantioselective Rh(I)-catalysed cyclisation of arylboron compounds onto ketones
Author: Wieczysty, Martin David
ISNI:       0000 0004 5991 7366
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2015
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1. C–H Functionalisation of 2 Aryl Cyclic 1,3-Dicarbonyl Compounds Two enolate-directed C–H functionalisation protocols have been developed using 2-aryl cyclic 1,3-dicarbonyl compounds as substrates. Reactions with activated alkenes, under ruthenium or palladium catalysis produced benzopyrans in most cases, in moderate to good yield. Alternatively, an oxidative annulation of 2-aryl cyclic 1.3-dicarbonyls with 1,3-enynes was facilitated under rhodium catalysis, forming functionalised spiroindene structures in most cases, in generally good yields and high regioselectivity. During the investigation, the serendipitous formation of spirodialin structures was also observed. 2. Enantioselective Rh(I)-Catalysed Cyclisation of Arylboron Compounds onto Ketones Chiral tertiary alcohols, bearing aza-, oxa- and carbocyclic core structures of varying ring size were successfully formed from arylboron substrates under rhodium catalysis. In general the reactions proceeded with good yield and with moderate to high enantioselectivity. A protocol for the formation of a bicyclic lactam system was also achieved in moderate yield and enantioselectivity.
Supervisor: Lam, Hon ; Lloyd-Jones, Guy Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: organic chemistry ; C–H functionalisation ; enantioselective