4008
J. M. Fraile et al. / Tetrahedron: Asymmetry 9 (1998) 3997–4008
catalyst is filtered off, washed with dichloromethane, and dried in the open air (the clays obtained from
CuI complexes are dried under argon). The recovered catalysts are reused, following the same method.
The results of the reactions are determined by gas chromatography, as described above.
The cyclopropanes were purified by column chromatography on silica gel, using n-hexane:ethyl
acetate (40:1) as an eluent, and their structures confirmed by 1H NMR.
Acknowledgements
This work was made possible by the generous financial support of the Comisión Interministerial de
Ciencia y Tecnología (Project MAT96-1053). One of us (T.T.) acknowledges the Spanish Ministerio
de Educación y Cultura for a post-doctoral fellowship. We are indebted to Laporte Adsorbents for the
generous gift of laponite.
References
1. Blaser, H.-U.; Pugin, B. In Chiral Reactions in Heterogeneous Catalysis; Jannes, G.; Dubois, V., Eds. Plenum Press: New
York, 1995; p. 33.
2. Blaser, H.-U. Tetrahedron: Asymmetry 1991, 28, 843.
3. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; p. 346.
4. Wan, K. T.; Davis, M. E. Nature 1994, 370, 449.
5. Sabater, M. J.; Corma, A.; Domenech, A.; Fornés, V.; García, H. Chem. Commun. 1997, 1285.
6. Ogunwumi, S. B.; Bein, T. Chem. Commun. 1997, 901.
7. Frunza, I.; Kosslick, H.; Landmesser, H.; Höft, E.; Fricke, R. J. Mol. Catal. A 1997, 123, 179.
8. Vankelecom, I. F. J.; Tas, D.; Parton, R. F.; Van de Vyver, V.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1346.
9. Janssen, K. B. M.; Laquiere, I.; Dehaen, W.; Parton, R. F.; Vankelecom, I. F. J.; Jacobs, P. A. Tetrahedron: Asymmetry
1997, 8, 3481.
10. Bedioui, F. Coord. Chem. Rev. 1995, 144, 39.
11. Thomas, J. M.; Teocharis, C. R. In Inclusion Compounds; Atwood, J. L.; Davies, J. E. D.; McNicol, D. D., Eds. Vol. 5.
Oxford University Press: Oxford, 1991; p. 104.
12. Yamaghisi, A. J. Coord. Chem. 1987, 16, 131.
13. Giannelis, E. P.; Rightor, E. G.; Pinnavaia, T. J. J. Am. Chem. Soc. 1988, 110, 3380.
14. Choudary, B. M.; Ravikumar, K.; Lakshmi, M. J. Catal. 1991, 130, 41.
15. Pinnavaia, T. J. ACS Symp. Ser. 1982, 192, 241.
16. Mazzei, M.; Marconi, W.; Riocci, M. J. Mol. Catal. 1980, 9, 381.
17. Shimazu, S.; Ro, K.; Sento, P.; Ichikuni, N.; Uematsu, T. J. Mol. Catal. A 1996, 107, 297.
18. Fraile, J. M.; García, J. I.; Massam, J.; Mayoral, J. A. J. Mol. Catal. A 1998, 136, 47.
19. For a recent review, see: Gosh, A. K.; Mathivanan, P.; Capiello, J. Tetrahedron: Asymmetry 1991, 9, 1.
20. Fraile, J. M.; García, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron: Asymmetry 1997, 8, 2089.
21. Pinnavaia, T. J. Science 1983, 220, 365.
22. Pinnavaia, T. J. In Chemical Physics of Intercalation; Legrand, A. P.; Flaudrois, S., Eds. NATO ASI Series, Series B, Vol.
172. Plenum Press: New York, 1987; p. 233.
23. Corey, E. J.; Imai, W.; Zhong, H. V. J. Am. Chem. Soc. 1991, 113, 728.
24. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
25. Pfaltz, A., personal communication.
26. Skordilis, C. S.; Pomonis, P. J. J. Mol. Catal. A 1995, 107, 191.
27. Datta Gupta, A.; Bhuniya, D.; Singh, V. K. Tetrahedron 1994, 50, 13725.
28. For a recent review on asymmetric cyclopropanation reactions, see: Singh, V. K.; Datta Gupta, A.; Sekar, G. Synthesis
1997, 137.
29. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
30. Fraile, J. M.; García, J. I.; Mayoral, J. A. Chem. Commun. 1996, 1319.