Date of Award


Degree Type


Degree Name

Master of Science




Dr. Nathan Jones


Due to their straightforward and modular syntheses and their capacity to effectively stabilize a range of transition metals, development of chiral, chelating ligand manifolds has dominated the field of asymmetric catalysis. This work describes the synthesis of two types of novel N,N,N- and C.iV-chelating, chiral ligands and their complexes with Pd(II) and Pt(II). Diastereomerically enriched chiral TVTVTV-chelating ligands were made that incorporated both oxazolidine and pyridine donors. In the presence of chloride anions, Pd(II) complexes of these ligands existed as rapidly exchanging bi- and tri-dentate isomers in solution. Exchange of Cl' for PFô' resulted in static tridentate coordination complexes. Achiral and chiral, C,7V-chelated pyridinylidene complexes of Pd(II) were also developed that rely on oxidative addition to Pd(0) of either chloropyridinium imines or aldehydes, respectively, and in the latter case subsequent Schiff base formation with chiral primary amines. These protocols succinctly circumvented many of the problems currently associated with the synthesis of chelating pyridinylidines.



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