Abstract
The oxidation of cobalt(II) chelate complexes [CoY] 2−, where Y=edta (ethylenediaminetetraacetate), pdta (1,2-propanediaminetetraacetate) and cydta ( trans-1,2-cyclohexanediaminetetraacetate), by [Co(mal) 3] 3− (mal=malonate) was catalyzed by chiral [Co(en) 3] 3+ to yield optically active products with the enantiomeric excesses which increase with increasing concentration of chiral [Co(en) 3] 3+. Substituents on the ethylenediamine backbone of [CoY] 2− had significant effects on the sign and the magnitude in the stereoselectivity. The results are interpreted in terms of a chiral induction mechanism in which the ion pair between [CoY] 2− and chiral [Co(en) 3] 3+ is stereoselectively oxidized by [Co(mal) 3] 3−. A model is proposed for the relative orientation of oxidant, reductant, and catalysis complexes.
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