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Title: Synthesis and applications of new chiral bipyridine libands.
Author: Sbircea, L.
ISNI:       0000 0001 3554 6562
Awarding Body: Queens University Belfast
Current Institution: Queen's University Belfast
Date of Award: 2008
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The projects concerns the preparation and applications of a new range of chiral ligands derivatives of 2,2'- and 4,4'- bipyridine. The synthetic route involves at first the enzymatic transformation of chloroquinoline derivatives substrates yielding enantiopure cis-dihydrodiols. These bioproducts were in tum converted in good yields to the corresponding enantiopure C-2 symmetric 2,2'-bipyridines, their 2,2'-bipyridine monoand di-N-oxides and the 4,4'-bipyridines via synthetic sequences including Ni(O)- mediated homocoupling and Suzuki heterocoupling processes. The chiral 2,2'-bipyridines ligands have been evaluated in a range of asymmetric reactions (i.e allylic oxidation, cyclopropanation, allylation, meso-epoxides ring opening) and have proved to be very stereoselective ligands (up to 97% ee). The first successful synthesis of a chiral metal-organic framework (MOF) in the series is based on solvothermal reaction of DMF solution of the enantiopure 4,4'-bipyridine ligand, fumaric acid and zinc nitrate hexahydrate. The asymmetric cavities of the MOF shown from X-ray crystal structure could be used to resolve enantiomeric mixtures. Enantiosorptions of various racemic mixtures (i.e. alcohols) by the newly synthesized chiral MOFs were attempted.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available