Supported chiral amino alcohols and diols functionalized with aluminium and titanium as catalysts of Diels-Alder reaction

Tetrahedron

Volumn 52, Issue 29, 1996, Pages 9853-9862

  Fraile, José M ^a   Mayoral, José A ^a   Royo, Ana J ^a   Salvador, Rosa V ^b   Altava, Belén ^b   Luis, Santiago V ^b   Burguete, María I ^b  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b ESTCE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; AMINOALCOHOL; POLYSTYRENE DERIVATIVE; PROLINOL; PYRROLIDINOL DERIVATIVE; TARTARIC ACID; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030586211     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00517-0     Document Type: Article

References (39)

1. 1. (a) Solid Supports and Catalysts in Organic Synthesis; Smith, K. Ed.; Ellis Horwood: Chichester, 1992.
2. (b) Syntheses and Separations using Functional Polymers, Sherrington, D.C.; Hodge, P.Eds.; John Wiley & Sons Inc.: New York, 1988.
3. 2. Blaser, H.U.; Pugin, B. In Chiral Reactions in Heterogeneous Catalysis; Jannes, G.; Dubois, J. Eds., Plenum Press: New York, 1995.
4. 3. (a) Tamioka, K. Synthesis 1990, 541.
5. (b) Narasaka, K. Synthesis 1991, 1.
6. (c) Kagan, H.B.; Riant, O. Chem. Rev. 1992, 92, 1007.
7. (d) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475 .
8. (e) Pindur, U.; Lutz, G.; Otto, C.Chem. Rev. 1993, 93, 742.
9. (f) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129.
10. (g) Waldmann, H. Synthesis 1994, 535.
11. 4. (a) Cativiela, C.; García, J.I.; Mayoral, J.A.; Pires, E.; Brown, R. Tetrahedron 1995, 51, 9217.
12. (b) Cativiela, C.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; Pires, E.; Royo, A.J.; Figueras, F.; de Ménorval, L.C. Tetrahedron 1993, 49, 4073.
13. (c) Luis, S.V.; Burguete, M.I.; Ramírez, N.; Mayoral, J.A.; Cativiela, C.; Royo, A.J. React. Polym. 1992, 18, 237.
14. (d) Cativiela, C.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; Figueras, F.; de Ménorval, L.C.; Alonso, P.J. J. Catal. 1992, 137, 394 and references cited therein.
15. 5. (a) Cativiela, C.; García, J.I.; Mayoral, J.A.; Pires, E.; Royo, A.J.; Figueras, F. Appl. Catal. A 1995, 131, 159.
16. (b) Cativiela, C.; García, J.I.; Mayoral, J.A.; Pires, E.; Royo, A.J.; Figueras, F. Tetrahedron 1995, 51, 1295.
17. (c) Cativiela, C.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; Pires, E.; Figueras, F.; de Ménorval, L.C. Tetrahedron 1992, 48, 6467.
18. (d) Cativiela, C.; Figueras, F.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; de Ménorval, L.C.; Pires, E. Appl. Catal. A 1993, 101, 253.
19. 6. (a) Cativiela, C.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; Pires, E.; Figueras, F. J. Mol. Catal. 1994, 89, 159.
20. (b) Cativiela, C.; Fraile, J.M.; García, J.I.; Mayoral, J.A.; Campelo, J.M.; Luna, D.; Marinas, J.M. Tetrahedron: Asymmetry 1993, 4, 2507.
21. (c) Cativiela, C.; Figueras, F.; García, J.I.; Mayoral, J.A.; Pires, E.; Royo, A.J. Tetrahedron: Asymmetry 1993, 4, 621.
22. (d) Cativiela, C.; Figueras, F.; Fraile, J.M.; García, J.I.; Mayoral, J.A. Tetrahedron: Asymmetry 1993, 4, 223.
23. (e) Kabalka, G.W.; Pagni, R.M.; Bains, S.; Hondrogiannis, G.; Plesco, M.; Kurt, R.; Cox, D.; Green, J. Tetrahedron: Asymmetry 1991, 2, 1283.
24. 7. (a) Itsuno, S.; Kamahori, K.; Watanabe, W,; Koizumi, F.; Ito, H. Tetrahedron: Asymmetry 1994, 5, 523.
25. (b) Kamahori, K.; Tado, S.; Ito, K.; Itsuno, S. Tetrahedron: Asymmetry 1995, 6, 2547.
26. 8. Cativiela, C.; García, J.I.; Mayoral, J.A.; Pires, E.; Royo, A.J. An. Quim, 1994, 90, 467.
27. 9. See for instance: (a) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem, Soc., Perkin Trans, 1 1984, 2887.
28. (b) Itsuno, S.; Nakano, M.; Ito, K.; Hirao, A.; Owa, M.; Kanda, S.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2615.
29. (c) Fréchet, J.M.J.; Bald, E.; Lecavalier, P. J. Org. Chem. 1986, 51, 3462.
30. (d) Itsuno, S.; Fréchet, J.M.J. J. Org. Chem. 1987, 52, 4140.
31. (e) Itsuno, S.; Sakurai, V.; Ito, K.; Hirao, A.; Nakahama, S. Bull. Chem. Soc. Jpn. 1987, 60, 395.
32. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 53, 927.
33. (g) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Fréchet, J.M.J. J. Org. Chem. 1990, 55, 304.
34. 10. Rebiere, F.; Riant, O.; Kagan, H.B. Tetrahedron: Asymmetry 1990, 1, 199.
35. 11. Ford, W.T. Site isolation organic synthesis in polystyrene networks. In Polymeric reagents and catalysts; Ford, W.T. Ed.; ACS Symposium Series, 308. ACS: Washington, 1986.
36. 12. Gung, B.W.; Yanik, M.M. J. Org. Chem. 1996, 61, 947.
37. 13. (a) Altava, B.; Burguete, M.I.; Luis, S.V.; Mayoral, J.A. Tetrahedron 1994, 50, 7535.
38. (b) Farrall, M.J.; Alexis, M.; Trecarten, M. Nouv. J. Chim. 1983, 7, 449.
39. 14. Darling, G.D.; Fréchet, J.M.J. J. Org. Chem. 1986, 51, 2270.