Abstract
Modified faujasites have been employed in order to incorporate sterically demanding organometallic complexes such as the Jacobsen catalyst in zeolites X and Y. The new heterogeneous catalysts have been tested in the diastereoselective epoxidation of (R)-(+)-limonene in the liquid phase in an autoclave at elevated pressure using O2 as the oxidant as well as in a glass reactor at ambient pressure using NaOCl as the oxidizing agent. In both catalytic systems conversions of 100% could be achieved. Selectivities were up to 70% and de values up to 55% in the autoclave experiments whereas in the experiments at atmospheric pressure they remained below 10 and 30%, respectively.
Similar content being viewed by others
References
K.J. Balkus, Jr., A.K. Khanmamedova, K.M. Dixon and F. Bedioui, Appl. Catal. A 143 (1996) 159.
E.N. Jacobsen, in: Catalytic Asymmetric Synthesis, ed. I. Ojima (VCH, New York, 1993) p. 159.
T. Katsuki, J. Mol. Catal. A 113 (1996) 87.
I.F.J. Vankelecom, D. Tas, R.F. Parton, V. Van de Vyver and P.A. Jacobs, Angew. Chem. 108 (1996) 1445.
M.J. Sabater, A. Corma, A. Domenech, V. Fornés and H. García, J. Chem. Soc. Chem. Commun. (1997) 1285.
W. Zhang and E.N. Jacobsen, J. Org. Chem. 56 (1991) 2296.
A. Robert, A. Tsapara and B. Meunier, J. Mol. Catal. 85 (1993) 13.
W. Adam, J. Jekö, A. Lévai, C. Nemes, T. Patonay and P. Sebök, Tetrahedron Lett. 36 (1995) 21, 3669.
T. Yamada, K. Imagawa, T. Nagata and T. Mukaiyama, Chem. Lett. (1992) 2231.
W. Kahlen, H.H. Wagner and W.F. Hölderich, Catal. Lett. 54 (1998) 85.
J.R. Sohn, S.J. DeCanio and J.H. Lunsford, Zeolites 6 (1986) 225.
H.K. Beyer and I. Belenykaja, in: Stud. Surf. Sci. Catal., Vol. 5, eds. B. Imelik et al. (Elsevier, Amsterdam, 1980) p. 203.
P.J. Grobet, P.A. Jacobs and H.K. Beyer, Zeolites 6 (1986) 47.
W. Lutz, E. Löffler and B. Zibrowius, in: Stud. Surf. Sci. Catal., Vol. 97, eds. L. Bonneviot and S. Kaliaguine (Elsevier, Amsterdam, 1995) p. 327.
N. Röhrlich, E. Löffler, B. Zibrowius, L. Chassot and W.F. Hölderich, J. Chem. Soc. Faraday Trans. 94 (1998) 609.
N.H. Lee, A.R. Muci and E.N. Jacobsen, Tetrahedron Lett. 32 (1991) 5055.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Heinrichs, C., Hölderich, W.F. Novel zeolitic hosts for “ship-in-a-bottle” catalysts. Catalysis Letters 58, 75–80 (1999). https://doi.org/10.1023/A:1019086102718
Issue Date:
DOI: https://doi.org/10.1023/A:1019086102718