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Chiral octahedral cobalt(III) complexes based on coordinated to metal ion chiral ligands are prospective catalysts providing a high stereoselective control in various asymmetric transformations. Here we introduce a library of the isostructural octahedral chiral-at-cobalt(III) complexes of Λ- and Δ-configurations based on Schiff’s bases of (R,R)-1,2-diaminocyclohexane and salicylaldehyde derivatives. The formation of a second Δ-diastereomer for this type of complexes has been observed for the first time. We found that the amount of Co(III) salt and the nature of the salicylaldehyde have a significant influence on the stereoselective assembly. We have demonstrated that the chirality at metal center has a perceptible effect on stereochemical outcome of reaction.