Synthesis and Characterization of New Chiral Schiff Base Complexes with Diiminobinaphthyl or Diiminocyclohexyl Moieties as Potential Enantioselective Epoxidation Catalysts |
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Authors: | Bernardo Katia Leppard Simon Robert Anne Commenges Gérard Dahan Françoise Meunier Bernard |
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Institution: | Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex, France. |
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Abstract: | New chiral Schiff base complexes have been obtained by condensation of 2,2'-diamino-1,1'-binaphthalene or 1,2-diaminocyclohexane and various salicylaldehydes and by subsequent metalation with manganese, iron, cobalt, nickel, copper, or zinc. The complete (1)H and (13)C NMR characterization of the ligands is reported, as are the X-ray crystal structures of (1R,2R)-(-)-N,N'-bis3-(N,N-dimethylamino)salicylidene]-trans-1,2-cyclohexanediimine and (1R,2R)-(-)-N,N'-bis(salicylidene)-trans-1,2-cyclohexanediiminato]copper(II). The new chiral manganese complexes have been evaluated in the oxygenation of prochiral olefins and sulfides using sodium hypochlorite, hydrogen peroxide, or N-methylmorpholine N-oxide/m-chloroperbenzoic acid as oxidant. |
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