Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Study of the Diastereoselectivity of Diels-Alder Reactions on the Ce-SiO2 as Support

  • Published : 2008.01.20
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Abstract

The diastereoselectivity of Diels-Alder reactions were studied on the silica surface supported with different concentrations of cerium ion as efficient Lewis acid catalysts under solvent-free conditions. The results showed that the diastereoselectivity of reaction was highly improved in these conditions. The cerium ion was grafted on silica surface by using ion exchange method.

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References

  1. Fringuelli, F.; Taticchi, A. Diels-Alder Reaction; Wiley: New York, 2002
  2. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990
  3. Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Eur. J. Org. Chem. 2001, 3, 439
  4. Kumar, A. Chem. Rev. 2001, 101, 1501 https://doi.org/10.1021/cr990363l
  5. Yates, P.; Eaton, P. J. Am. Chem. Soc. 1960, 82, 4436 https://doi.org/10.1021/ja01501a085
  6. Inukai, T.; Kojima, T. J. Org. Chem. 1971, 36, 924 https://doi.org/10.1021/jo00806a014
  7. Alves, C. N.; da Silva, A. B. F.; Marti, S.; Moliner, V.; Oliva, M.; Andres, J.; Domingo, L. R. Tetrahedron 2002, 58, 2695 https://doi.org/10.1016/S0040-4020(02)00072-8
  8. Weinstein, D.; Rensle, R.; Danheiser, L.; Tester, W. J. Phys. Chem. 1999, B103, 2876
  9. Pearson, R. G. Hard and Soft Acids and Bases; Hutchinson & Ross: Stroundsburg, 1973
  10. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287
  11. Furuno, H.; Hayano, T.; Kambara, T.; Sugimato, Y.; Hanamoto, T.; Tanaka, Y.; Zhi Jin, Y.; Hagawa, T.; Inanaga, J. Tetrahedron 2003, 59, 10509 https://doi.org/10.1016/j.tet.2003.06.011
  12. Mahmoudi Najafi, H.; Gandi, M.; Farzaneh, F. Chem. Lett. 2000, 358
  13. Liu, J.; Yin, D.; Yin, D.; Fu, Z.; Li, Q.; Lu, G. J. Mol. Catal , 2004, A209, 171
  14. Onka, M.; Hashimoto, N.; Yamasaki, R.; Kibata, Y. Chem. Lett. 2002, 166
  15. Onka, M.; Hashimoto, N.; Kibata, Y.; Yamasaki, R. Appl. Catal. 2003, A241, 307
  16. Sreekanth, P.; Kim, S.; Hyeon, T.; Kima, B. M. Adv. Synth. Catal. 2003, 345, 936 https://doi.org/10.1002/adsc.200303061
  17. Fraile, J. M.; Garcia, J.; Mayoral, J. A.; Grazia Proietti, M.; Sanchez, M. C. J. Phys. Chem. 1996, 100, 19484 https://doi.org/10.1021/jp961487u
  18. Chavan, S. P.; Sharma, A. K. Synlett 2001, 5, 667
  19. Clark, J. H. Supported Reagents in Organic Reactions; VCH: Weinheim, 1994
  20. Iler, R. K. The Chemistry of Silica, Solubility, Polymerization, Colloid and Surface Propertie, and Biochemistry; John Wiley & Sons: New York, 1979
  21. Badiei, A.; Mohammadi Ziarani, G.; Norouzi, P.; Tousi, F. Iranian International J. Sci. 2004, 5, 31
  22. Che, M.; Bonneviot, L. Pure Appl. Chem. 1988, 60, 1369 https://doi.org/10.1351/pac198860081369
  23. Cho, I.; Ahn, K.-D. Journal of the Korean Chemical Society 1976, 20, 299
  24. Veselovsky, V. V.; Lozanova, S. A. L.; Moiseenkov, A. M.; Smith, W. A.; Caple, R. Tetrahedron Letters 1988, 29, 175 https://doi.org/10.1016/S0040-4039(00)80045-3
  25. Veselovskii, V. V.; Gybin, A. S.; Lozanova, A. V.; Moiseenko, A. M.; Smith, W. A. Bull. Acad. Sci. USSR 1990, 107
  26. Menger, F. M. Acc. Chem. Res. 1985, 18, 128 https://doi.org/10.1021/ar00113a001
  27. Parlar, H.; Baumann, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 1014

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