Effect of substrate and catalyst chirality on the diastereoselective epoxidation of R-(+)-limonene with manganese(III) salen complexes

  • Juliana Reyes Universidad de Antioquia
  • Jairo Antonio Cubillos Universidad de Antioquia
  • Aída Luz Villa Universidad de Antioquia
  • Consuelo Montes de Correa Universidad de Antioquia
Keywords: R-( )-limonene, enantiomerically pure epoxides, asymmetric synthesis, manganese (III) salen complexes, optically active catalysts, achiral catalyst

Abstract

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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Author Biographies

Juliana Reyes, Universidad de Antioquia

Grupo Catálisis Ambiental, Facultad de Ingeniería

Jairo Antonio Cubillos, Universidad de Antioquia

Grupo Catálisis Ambiental, Facultad de Ingeniería

Aída Luz Villa, Universidad de Antioquia

Grupo Catálisis Ambiental, Facultad de Ingeniería

Consuelo Montes de Correa, Universidad de Antioquia

Grupo Catálisis Ambiental, Facultad de Ingeniería

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Published
2013-07-23
How to Cite
Reyes J., Cubillos J. A., Villa A. L., & Montes de Correa C. (2013). Effect of substrate and catalyst chirality on the diastereoselective epoxidation of R-(+)-limonene with manganese(III) salen complexes. Revista Facultad De Ingeniería Universidad De Antioquia, (48), 18-26. Retrieved from https://revistas.udea.edu.co/index.php/ingenieria/article/view/16005