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MCM-41 Heterogenized Chiral Amines as Base Catalysts for Enantioselective Michael Reaction

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Abstract

Cinchonidine and cinchonine have been grafted onto pure silica MCM-41. It has been shown that both supported alkaloids are active catalysts for the Michael addition of ethyl 2-oxocyclopentanecarboxylate and methyl vinyl ketone, anchored cinchonidine being more active and enantioselective than anchored cinchonine. The study of the influence of the polarity of the solvent and reaction temperature on the optical induction shows that there is not a direct correlation between solvent polarity and enantioselectivity, and the maximum optical yield was obtained between 278 and 273 K.

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References

  1. S.C. Stinson, Chem. Engng News 28 (1992) 46.

    Google Scholar 

  2. G.M. Ramos Tombo and D. Bellus, Angew. Chem. 103 (1991) 1219.

    Google Scholar 

  3. R. Noyori, ChemTech 22 (1992) 366.

    Google Scholar 

  4. J.F. Nicoud and R.J. Twieg, in: Nonlinear Optical Properties of Organic Molecules and Crystals, eds. D.S. Chemla and J. Zyss (Academic Press, Orlando, 1987) p. 227.

    Google Scholar 

  5. H.U. Blaser, Chem. Rev. 92 (1992) 935.

    Google Scholar 

  6. R.A. Sheldon, Chirotechnology (Marcel Dekker, New York, 1993).

    Google Scholar 

  7. A. Tungler, T. Mathe, J. Petro and T. Tarnai, J. Mol. Catal. 61 (1990) 259; A. Tungler, T. Mathe, J. Petro and T. Tarnai, J. Mol. Catal. 67 (1991) 277; H.U. Blaser, Tetrahedron Asym. 2 (1991) 843; B. Minder, T. Mallat, P. Skrabal and A. Baiker, Catal. Lett. 29 (1994) 115; B. Minder, T.M. Shürch, T. Mallat and A. Baiker, Catal. Lett. 31 (1995) 143.

    Google Scholar 

  8. S. Itsuno and J.M.J. Frechet, J. Org. Chem. 52 (1987) 4140; K. Soai, S. Niwa and M. Watanabe, J. Org. Chem. 53 (1988) 927.

    Google Scholar 

  9. M.J. Sabater, A. Corma, A. Doménech, V. Fornés and H. García, Chem. Commun. (1997) 1285; S.B. Ogunwuni and T. Bein, Chem. Commun. (1997) 901.

  10. A. Corma, M. Iglesias, C. del Pino and F. Sánchez, J. Chem. Soc., Chem. Commun. (1991) 1253.

  11. A. Corma, M. Iglesias, C. del Pino and F. Sánchez, J. Organomet. Chem. 431 (1992) 233.

    Google Scholar 

  12. A. Corma, M. Iglesias, J.P. Obisco and F. Sánchez, in: Chiral Reactions in Heterogeneous Catalysis, eds. G. Jannes and V. Dubois (Plenum Press, New York and London, 1995) p. 179.

    Google Scholar 

  13. U. Nagel and E. Kingel, J. Chem. Soc., Chem. Commun. (1986) 1098.

  14. K. Sosai, M. Watanabe and A. Yamamoto, J. Org. Chem. 55 (1990) 4832.

    Google Scholar 

  15. D. Brunel and P. Sutra, in: 3rd International Symposium on Supported Reagents and Catalysts in Chemistry (Royal Society of Chemistry, Limerick, Ireland, 1998) p. 54.

    Google Scholar 

  16. M. Lasperas, N. Bellocq, D. Brunel and P. Moreau, Tetrahedron Asym. 9 (1998) 3053.

    Google Scholar 

  17. N. Bellocq, D. Brunel, M. Lasperas and P. Moreau, Stud. Surf. Sci. Catal. 108 (1997) 485.

    Google Scholar 

  18. S. Abramson, M. Lasperas, A. Galarneau, D. Desplantier-Giscard and D. Brunel, Chem. Commun. (2000) 1773.

  19. B. Langstrom and G. Bergson, Acta Chem. Scand. 27 (1973) 3118.

    Google Scholar 

  20. B.E. Rossiter and N.M. Swingle, Chem. Rev. 92 (1992) 771.

    Google Scholar 

  21. Y. Tamai, A. Kamifuku, E. Koshiishi and S. Miyano, Chem. Lett. (1995) 957, and references cited therein; R. Noyori, in: Asymmetric Catalysis in Organic Synthesis (Wiley, New York, 1994) p. 241; M. Wills and H. Tye, J. Chem. Soc., Perkin Trans. I (1999) 1109.

  22. H. Sasai, T. Arai, Y. Satow, K.N. Houk and M. Shibasaki, J. Am. Chem. Soc. 117 (1995) 6194.

    Google Scholar 

  23. P. Bakó, L. Töke, A. Szöllösy and P. Bombicz, Heteroatom. Chem. 8 (1997) 333.

    Google Scholar 

  24. P. Bakó, Z. Bajor and L. Töke, J. Chem. Soc., Perkin Trans. 1 (1999) 3651.

    Google Scholar 

  25. P. Bakó, T. Kiss and L. Töke, Tetrahedron Lett. 38 (1997) 7259.

    Google Scholar 

  26. D.J. Cram and G.D.Y. Sogah, J. Chem. Soc., Chem. Commun. 13 (1981) 625.

    Google Scholar 

  27. H. Wynberg and R. Helder, Tetrahedron Lett. (1975) 4057; (b) K. Hermann and H. Wynberg, J. Org. Chem. 44 (1979) 2738; (c) H. Brunner and B. Hammer, Angew. Chem. Int. Ed. Engl. 23 (1984) 312; (d) H. Brunner and C. Krumey, J. Mol. Catal. 142 (1999) 7; (e) A. Latvala, S. Stanchev, A. Linden and M. Hesse, Tetrahedron Asym. 4 (1993) 173.

  28. M. Iglesias-Hernández and F. Sánchez-Alonso, Stud. Surf. Sci. Catal. 130 (2000) 3393.

    Google Scholar 

  29. C. Krumey, PhD Thesis, University of Regensburg, 1995.

  30. H. Buschmann, H.D. Scharf, N. Hoffmann and P. Esser, Angew. Chem. Int. Ed. Engl. 30 (1991) 477; (b) D. Heller, H. Buschmann and H.D. Scharf, Angew. Chem. Int. Ed. Engl. 35 (1996) 1852; (c) H. Zhang and K.S. Chan, J. Chem. Soc., Perkin Trans. I (1999) 381; (d) V.V. Krotov, S.M. Staroverov, P.N. Nesterenko and G.V. Lisichkin, Zh. Obshch. Khim. 57 (1987) 1187. (e) B. Giese, Angew. Chem. Ed. Int. Eng. 16 (1977) 125; (f) H.D. Scharf, J. Am. Chem. Soc., 111 (1989) 5367; (g) K. J. Hale and J.H. Ridd, J. Chem. Soc., Chem. Commun. (1995) 357.

    Google Scholar 

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Corma, A., Iborra, S., Rodríguez, I. et al. MCM-41 Heterogenized Chiral Amines as Base Catalysts for Enantioselective Michael Reaction. Catalysis Letters 82, 237–242 (2002). https://doi.org/10.1023/A:1020531315091

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