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Title: Chiral N-heterocyclic carbenes as ligands for boron-mediated asymmetric processes
Author: McArthur , David
ISNI:       0000 0004 2675 7909
Awarding Body: University of Bristol
Current Institution: University of Bristol
Date of Award: 2009
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N-heterocyclic carbenes (NHCs) have emerged over the last two decades as an important class of ligands in transition metal complexes, main group chemistry and organocatalysis. NHCs are now common replacements for phosphines in transition metal chemistry. This thesis describes the synthesis of a variety of chiral NHCs mainly derived from a series of bis(oxazolines) prepared from 1,2-amino acids. These imidazolium salts were then deprotonated to from the corresponding carbenes and complexed with various boranes to form novel chiral NHC borane complexes. The ability for these complexes to perform an asymmetric reduction of acetophenone has been extensively investigated, The optimum complex has been used to reduce a selection of prochiral ketones in up to 85 % ee in the presence of a Lewis acid.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available