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Title: Copper and iridium conjugate addition : cyclisation processes, domino reactions
Author: Solana González, Jorge
ISNI:       0000 0004 5347 869X
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2015
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Asymmetric conjugate addition of bis(pinacolato)diboron followed by aldol cyclisation of enone diones under the action of a chiral copper catalyst has been developed. This enantioselective process, using a chiral bisphosphine as ligand, allows the formation of bicyclic alcohols with four contiguous stereocentres in high diastero- and enantioselectivity. This catalytic system has been applied to the parallel kinetic resolution of a racemic β- ketoamide. Further functionalization of the bicyclic alcohols synthesised was also possible. A domino addition of arylboronic acids and cyclisation of alkynones via an undescribed iridium 1-4-migration process has been developed. A range of tricyclic compounds using a variety of arylboronic acids have been synthesised in good yields and high diasteroselectivity. The use of chiral bisphosphine ligand together with an iridium salt allows the formation of enantioenriched compounds in moderate yield.
Supervisor: Bradley, Mark; Lam, Hon; Hulme, Alison Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: domino reactions ; iridium ; copper ; borylation