Effect of substrate and catalyst chirality on the diastereoselective epoxidation of R-(+)-limonene with manganese(III) salen complexes
Keywords:R-( )-limonene, enantiomerically pure epoxides, asymmetric synthesis, manganese (III) salen complexes, optically active catalysts, achiral catalyst
The asymmetric epoxidation of R-(+)-limonene in the presence of the Jacobsen´s catalyst in its chiral and achiral either homogeneous or heterogeneous (immobilized on Al-MCM-41) forms was studied using in situ generated dimethyldioxirane as oxidizing agent. It was found that the catalytic activity of the chiral and achiral forms of the Jacobsen´s catalyst was very similar either homogeneous or heterogeneous. This result suggests that the preferential formation of cis-(+)-1,2-limonene oxide depends not only on the catalyst chiral center, but also on the substrate chiral center. This represents a clear advantage from the economical point of view since the achiral catalyst is much less expensive than its chiral counterpart.
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