Copper and iridium conjugate addition – cyclisation processes; domino reactions
dc.contributor.advisor
Bradley, Mark
en
dc.contributor.advisor
Lam, Hon
en
dc.contributor.advisor
Hulme, Alison
en
dc.contributor.author
Solana González, Jorge
en
dc.contributor.sponsor
Engineering and Physical Sciences Research Council (EPSRC)
en
dc.date.accessioned
2015-07-09T14:21:35Z
dc.date.available
2015-07-09T14:21:35Z
dc.date.issued
2015-06-30
dc.description.abstract
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.
en
dc.identifier.uri
http://hdl.handle.net/1842/10471
dc.language.iso
en
dc.publisher
The University of Edinburgh
en
dc.relation.references
Enantioselective Copper(I)-Catalyzed Borylative Aldol Cyclizations of Enone– Diones, A. R. Burns, J. Solana González, H. W. Lam, Angewandte Chemie International Edition 2012, 51, 10827-10831.
en
dc.relation.references
Iridium-Catalyzed Arylative Cyclization of Alkynones by 1,4-Iridium Migration, B. M. Partridge, J. Solana González, H. W. Lam, Angewandte Chemie International Edition 2014, 53, 6523-6527.
en
dc.rights
Attribution-NonCommercial-ShareAlike 4.0 International
en
dc.rights.uri
http://creativecommons.org/licenses/by-nc-sa/4.0/
dc.subject
domino reactions
en
dc.subject
iridium
en
dc.subject
copper
en
dc.subject
borylation
en
dc.title
Copper and iridium conjugate addition – cyclisation processes; domino reactions
en
dc.type
Thesis or Dissertation
en
dc.type.qualificationlevel
Doctoral
en
dc.type.qualificationname
PhD Doctor of Philosophy
en
This item appears in the following Collection(s)