Asymmetric cyclopropanation catalysed by cationic bis(oxazoline)-Cu(II) complexes exchanged into clays

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2089-2092

  Fraile, José M ^a   García, José I ^a   Mayoral, José A ^a   Tarnai, Tibor ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030862579     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00242-5     Document Type: Article

References (31)

1. Blaser, H.-U.; Pugin, B. in "Chiral Reactions in Heterogeneous Catalysis", Jannes, G. and Dubois, V., Eds., p. 33, Plenum Press, New York, 1995.
2. (a) Blaser, H.-U. Tetrahedron: Asymmetry 1991, 3, 843.
3. (b) Noyori, R. "Asymmetric Catalysis in Organic Synthesis", p. 346, Wiley, New York, 1994.
4. Vankelecom, I. F. J.; Tas, D.; Parton, R. F.; van de Vyver, V.; Jacobs, P. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1346.
5. (a) Bedioui, F. Coord. Chem. Rev. 1995, 144, 39.
6. (b) Thomas, J. M.; Theocharis, C. R., in "Inclusion Compounds", Vol. 5, Atwood, J. L., Davies, J. E. D. and MacNicol, D. D., Eds., p. 104, Oxford University Press, Oxford, 1991.
7. (c) Yamaghisi, A. J. Coord. Chem. 1987, 16, 131.
8. (d) Giannelis, E. P.; Rightor, E. G.; Pinnavaia, T. J. J. Am. Chem. Soc. 1988, 110, 3380.
9. (e) Choudary, B. M.; Ravikumar, K.; Lakshmi Kantam, M. J. Catal. 1991, 130, 41.
10. (a) Pinnavaia, T. J. ACS Symp. Ser. 1982, 192, 241.
11. (b) Mazzei, M.; Marconi, W.; Riocci, M. J. Mol. Catal. 1980, 9, 381.
12. (c) Shimazu, S.; Ro, K.; Sento, P.; Ichikuni, N.; Uematsu, T. J. Mol. Catal. A, 1996, 107, 297.
13. For leading examples, see: (a) Itsuno, S.; Yoshiki, S.; Kiochi, I.; Toshihiro, M.; Seiichi, N.; Frechet, J. M. J. J. Org. Chem. 1990, 55, 304.
14. (b) Itsuno, S.; Frechet, J. M. J. J. Org. Chem. 1987, 52, 4140.
15. For leading examples, see: (a) Parrinello, G.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122.
16. (b) Parrinello, G.; Deschenaux, R.; Stille, J. K. J. Org. Chem. 1986, 51, 4189.
17. (a) Martin, S. A.; Lough, W. J.; Chan, L.; Abram, D. M. H.; Zhou, Z. J. Chem. Soc., Chem. Commun. 1984, 1038.
18. (b) Doyle, M. P.; Eismont, M. Y.; Beregbreiter, D. E.; Gray, H. N. J. Org. Chem. 1992, 57, 6103.
19. (c) Oudejans, J. C.; Kamisnka, J.; Kock-van-Dalen, A. C.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1986, 105, 421.
20. (a) Itsuno, S.; Kamahori, K.; Watanabe, K.; Koizumi, T.; Ito, K. Tetrahedron: Asymmetry 1994, 5, 523.
21. (b) Kamahori, K.; Tada, S.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 2547.
22. (c) Fraile, J. M.; García, J. I.; Mayoral, J. A.; Royo, A. J. Tetrahedron: Asymmetry 1996, 7, 2263.
23. (d) Fraile, J. M.; Mayoral, J. A.; Royo, A. J.; Salvador, R. V.; Altava, B.; Luis, S. V.; Burguete, M. I. Tetrahedron 1996, 52, 9853.
24. (e) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710.
25. (f) Altava, B.; Burguete, M. I.; Escuder, B.; Luis, S. V.; Salvador, R. V.; Fraile, J. M.; Mayoral, J. A.; Royo, A. J. J. Org. Chem., 1997, 62, 3126.
26. For a review on catalytic enantioselective cyclopropanation, see: Singh, V. K.; Gupta, A. D.; Sekar, G. Synthesis 1997, 137.
27. Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
28. 3a, Prof. Pfaltz, personal communication. 3b, Corey, E. J.; Imai, W.; Zhang, H. Y. J. Am. Chem. Soc. 1991, 113, 728.
29. Fraile, J. M.; García, J. I.; Mayoral, J. A. Chem. Commun. 1996, 1319.
30. Johansen, M.; Jørgensen, K. A. Tetrahedron 1996, 52, 7321.
31. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.