Within the field of asymmetric catalysis, chiral paddle-wheel dirhodium(II) complexes have proven to be highly effective in numerous highly selective reactions. Rhodium, however, is very costly which has resulted in exploration into whether alternative transition metals could act similarly when used in asymmetric catalysis with chiral paddle-wheel complexes. Recent studies have shown ruthenium complexes to be promising. The objective of this work is to determine the efficiency of the enantiopure paddle-wheel diruthenium complex [Ru2Cl((-)2-pycsa)2(O2CMe)2]. The structure features a diruthenium core to which are coordinated a single chloride ligand, two enantiopure camphor-based pyridyl sulfonamido ligands, and two acetate ligands in a paddle-wheel configuration. The diruthenium complex was applied as the catalyst in three reactions, which included an asymmetric hetero Diels-Alder reaction and an intramolecular C-H amination reaction where the complex acted as a Lewis acid. These reaction were monitored by 1H NMR to determine the catalytic efficiency. The diruthenium complex was also used to facilitate the oxygenation of sulfides by tert-butyl hydroperoxide. This reaction was monitored by GC to determine the progression of the oxygenation from sulfide to sulfoxide and sulfone. Analysis of the results showed low catalytic activity with respect to the state of the art in each case.

Chiral paddle-wheel diruthenium complexes for asymmetric catalysis

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