Enantioselective hydrogenation of pyrrolidine-2,3,5-triones over the Pt- cinchonidine system

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 61-76

  Szabo, A ^a   Kunzle N ^a   Mallat, T ^a   Baiker, A ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; CINCHONIDINE; PLATINUM; PYRROLIDIN 2,3,5 TRIONE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL;

EID: 0039528130     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00499-6     Document Type: Article

References (39)

1. (a) Noyori, R. Chem. Soc. Rev., 1989, 187-208;
2. (b) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev., 1992, 92, 1051-1069;
3. (c) Takaya, M.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp. 1-39.
4. (a) Izumi, Y. Adv. Catal., 1983, 32, 215-271;
5. (b) Blaser, H. U. Tetrahedron: Asymmetry, 1991, 2, 843-866;
6. (c) Webb, G.; Wells, P. B. Catal. Today, 1992, 12, 319-338;
7. (d) Baiker, A. J. Mol. Catal. A: Chem., 1997, 115, 473-493;
8. (e) Osawa, T.; Harada, T.; Tai, A. Catal. Today, 1997, 37, 465-480.
9. (a) Orito, Y.; Imai, S.; Niwa, S.; Nguyen, G.-H. J. Synth. Org. Chem. Jpn., 1979, 37, 173-174;
10. (b) Orito, Y.; Imai, S.; Niwa, S. J. Chem. Soc. Jpn., 1979, 1118-1120.
11. Zao, X.; Liu, H. Tetrahedron Lett., 1998, 39, 1941-1944.
12. Blaser, H. U.; Jalett, H. P. Stud. Surf. Sci. Catal., 1993, 78, 139-146.
13. (a) Schüren, M.; Schwalm, O.; Mallat, T.; Weber, J.; Baiker, A. J. Catal., 1997, 169, 275-286;
14. (b) Schüren, M.; Künzle, N.; Mallat, T.; Baiker, A. J. Catal., 1998, 176, 569-571.
15. (a) Vermeer, W. A. H.; Fulford, A.; Johnston, P.; Wells, P. B. J. Chem. Soc., Chem. Commun., 1993, 1053-1056;
16. (b) Mallat, T.; Bodmer, M.; Baiker, A. Catal. Lett., 1997, 44, 95-99;
17. (c) Wang, G.-Z.; Mallat, T.; Baiker, A. Tetrahedron: Asymmetry, 1997, 8, 2133-2140.
18. Künzle, N.; Szabo, A.; Schürch, M.; Mallat, T.; Baiker, A. Chem. Commun., 1998, 1377-1378.
19. (a) Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett., 1985, 3095-3098;
20. (b) Poll, T.; Abdel Hady, A. F.; Karge, R.; Linz, G.; Weetman, J.; Helmchen, G. Tetrahedron Lett., 1989, 30, 5595-5598.
21. Corey, E. J.; Schmidt, G. Tetrahedron Lett., 1979, 5, 399-402.
22. (a) Skinner, G. S.; Perkins Jr., J. F. J. Am. Chem. Soc., 1950, 72, 5569-5573;
23. (b) Sheehan, J. C.; Corey, E. J. J. Am. Chem. Soc., 1952, 74, 360-365;
24. (c) Skinner, G. S.; Miller, C. B. J. Am. Chem. Soc., 1953, 75, 977-979;
25. (d) Skinner, G. S.; Ludwig, R. E. J. Am. Chem. Soc., 1956, 78, 4656-4659.
26. Blaser, H.-U.; Jalett, H.-P.; Müller, M.; Studer, M. Catal. Today, 1997, 37, 441-467.
27. Reichhardt, C. In Solvents and Solvent Effects in Organic Chemistry, Ebel, H. F., Ed.; VCH: Weinheim/New York, 1988; pp. 241-246.
28. Bürgi, T.; Baiker, A. J. Am. Chem. Soc., 1998, submitted for publication.
29. (a) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc., 1989, 111, 8069-8076;
30. (b) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H. Recl. Trav. Chim. Pays-Bas, 1989, 108, 195-204;
31. (c) Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H. J. Org. Chem., 1990, 55, 6121-6131.
32. Mallat, T.; Bodnar, Z.; Minder, B.; Borszeky, K.; Baiker, A. J. Catal., 1997, 168, 183-193.
33. Meheux, P. A.; Ibbotson, A.; Wells, P. B. J. Catal., 1991, 128, 387-396.
34. Blaser, H. U.; Jalett, H. P.; Monti, D. M.; Reber, J. F.; Wehrli, J. T. Stud. Surf. Sci. Catal., 1988, 41, 153-163.
35. Delbecq, F.; Sautet, P. Surf. Sci., 1993, 295, 353-373.
36. (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem., 1969, 34, 2543-2549;
37. (b) Kalyanam, N.; Lightner, D. A. Tetrahedron Lett., 1979, 5, 415-418.
38. Hata, H.; Morishita, T.; Akutsu, S.; Kawamura, M. Synthesis, 1991, 4, 289-291.
39. Ito, M.; Kibayashi, C. Synthesis, 1993, 1, 137-140.