Synthesis of chiral catalyst modifiers by hydrosilylation of cinchonidine and their application in the hydrogenation of 1-phenylpropane-1,2-dione and ethyl pyruvate on a supported Pt/Al2O3 catalyst

European Journal of Organic Chemistry

Volumn , Issue 13, 2005, Pages 2811-2821

  Busygin, Igor ^a   Toukoniitty, Esa ^b   Sillanpää, Reijo ^c   Murzin, Dmitry Yu ^b   Leino, Reko ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b LABORATORY OF INDUSTRIAL CHEMISTRY AND REACTION ENGINEERING   (Finland)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Cinchonidine; Heterogeneous catalysis; Hydrogenation; Hydrosilylation; Platinum

Indexed keywords

EID: 22144468070     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500161     Document Type: Article

References (74)

1. For reviews, see: a) G. Webb, P. B. Wells, Catal. Today 1992, 12, 319-337;
2. b) M. Studer, H.-U. Blaser, C. Exner, Adv. Synth. Catal. 2003, 345, 45-65;
3. c) M. E. Davis, Micropor. Mesopor. Mater. 1998, 21, 173-182;
4. d) P. B. Wells, A. G. Wilkinson, Top. Catal. 1998, 5, 39-50;
5. e) H. Brunner, W Zettlmeier, Handbook of Enantioselective Catalysis, VCH, Weinheim, 1993;
6. f) J. M. Brown, in Comprehensive Asymmetric Catalysis (Ed.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999.
7. For reviews, see: a) A. Baiker, J. Mol. Catal. A: Chem. 1997, 115, 473-493;
8. b) H. U. Blaser, H. P. Jalett, M. Müller, M. Studer, Catal. Today 1997, 37, 441-443;
9. c) P. B. Wells, P. K. Wells, in Chiral Catalyst Immobilization and Recycling (Eds.: D. E. DeVos, I. F. J. Vankelecom, P. A. Jacobs), Wiley-VCH, Weinheim, 2000, 123;
10. d) M. von Arx, T. Mallat, A. Baiker, Top. Catal. 2002, 19, 75-87.
11. M. Sutyinszki, K. Szöri, K. Felföldi, M. Bartók, Catal. Commun. 2002, 3, 125-127.
12. See, for example: a) J. Kubota, F. Zaera, J. Am. Chem. Soc. 2001, 123, 11115-11116;
13. b) D. Ferri, T. Bürgi, J. Am. Chem. Soc. 2001, 123, 12074-12084;
14. c) N. Bonalumi, T. Bürgi, A. Baiker, J. Am. Chem. Soc. 2003, 125, 13342-13343;
15. d) J. M. Bonello, F. J. Williams, R. M. Lambert, J. Am. Chem. Soc. 2003, 125, 2723-2729;
16. e) G. Vayner, K. N. Houk, Y.-K. Sun, J. Am. Chem. Soc. 2004, 126, 199-203.
17. In addition to the surface adsorption model, a chemical shielding model based on the formation of a complex between the modifier and reactant in the liquid face has been proposed by Margitfalvi and co-workers. Formation of such a complex between ethyl pyruvate and cinchonidine in solution has been confirmed by NMR spectroscopy. See, for example: a) J. L. Margitfalvi, M. Hegedüs, J. Mol. Catal. A: Chem. 1996, 107, 281-289;
18. b) J. L. Margitfalvi, E. Tálas, E. Tfirst, C. V. Kumar, A. Gergely, Appl. Catal., A 2000, 191, 177-191. However, since the enantioselective hydrogenation is sensitive to the properties of the catalyst per se the metal surface including the adsorption-desorption phenomena should be taken into account explicitly in the mechanistic proposals.
19. a) H. U. Blaser, H. P. Jalett, W. Lottenbach, M. Studer, J. Am. Chem. Soc. 2000, 122, 12675-12682;
20. b) C. Exner, A. Pfaltz, M. Studer, H.-U. Blaser, Adv. Synth. Catal. 2003, 345, 1253-1260;
21. c) K. E. Simons, G. Wang, T. Heinz, T. Giger, T. Mallat, A. Pfaltz, A. Baiker, Tetrahedron: Asymmetry 1995, 6, 505-518;
22. d) B. Minder, T. Mallat, A. Baiker, G. Wang, T. Heinz, A. Pfaltz, J. Catal. 1995, 154, 371-378;
23. e) B. Minder, M. Schürch, T. Mallat, A. Baiker, T. Heinz, A. Pfaltz, J. Catal. 1996, 160, 261-268;
24. f) A. Pfaltz, T. Heinz, Top. Catal. 1997, 4, 229-239;
25. g) M. Schürch, T. Heinz, R. Aeschimann, T. Mallat, A. Pfaltz, A. Baiker, J. Catal. 1998, 173, 187-195.
26. a) M. Garland, H. U. Blaser, J. Am. Chem. Soc. 1990, 112, 7048-7050;
27. b) H. U. Blaser, M. Garland, H. P. Jallett, J. Catal. 1993, 144, 569-578;
28. c) H. U. Blaser, D. Imhof, M. Studer, Stud. Surf. Sci. Catal. 1997, 108, 175-182;
29. d) M. Bartok, K. Balazsik, T. Bartok, Z. Kele, Catal. Lett. 2003, 87, 235-240.
30. a) J. L. Margitfalvi, M. Hegedüs, J. Mol. Catal. A: Chem. 1996, 107, 281-289;
31. b) J. L. Margitfalvi, E. Tálas, M. Hegedûs, Chem. Commun. 1999, 645-646;
32. c) R. P. K. Wells, N. R. McGuire, X. Li, R. L. Jenkins, P. J. Collier, R. Whyman, G. J. Hutchings, Phys. Chem. Chem. Phys. 2002, 4, 2839-2845.
33. a) H. U. Blaser, H. P. Jalett, D. M. Monti, J. T. Wehrli, Appl. Catal. 1989, 52, 19-32;
34. b) B. Minder, T. Mallat, P. Skrabal, A. Baiker, Catal. Lett. 1994, 29, 115-124;
35. c) T. Mallat, Catal. Lett. 1999, 63, 121-126;
36. d) X. Li, R. P. K. Wells, P. B. Wells, G. J. Hutchings, Catal. Lett. 2003, 89, 163-167.
37. a) J. T. Wehrli, A. Baiker, D. M. Monti, H. U. Blaser, J. Mol. Catal. 1989, 49, 195-203;
38. b) J. T. Wehrli, A. Baiker, D. M. Monti, H. U. Blaser, J. Mol. Catal. 1990, 61, 207-226;
39. c) H. U. Blaser, H. P. Jalett, D. M. Monti, A. Baiker, J. T. Wehrli, Stud. Surf. Sci. Catal. 1991, 67, 147-155.
40. a) J. T. Wehrli, A. Baiker, D. M. Monti, H.-U. Blaser, H. P. Jalett, J. Mol. Catal. 1989, 57, 245-257;
41. b) H.-U. Blasser, H. P. Jallet, J. T. Wehrli, J. Mol. Catal. 1991, 68, 215-222.
42. [2] and references cited therein.
43. a) Y. Sun, R. N. Landau, J. Wang, C. LeBlond, D. G. Blackmond, J. Am. Chem. Soc. 1996, 118, 1348-1353;
44. b) J. Wang, C. Leblond, C. F. Orella, Y. Sun, J. S. Bradley, D. G. Blackmond, Stud. Surf. Sci. Catal. 1997, 108, 183-190.
45. a) E. Toukoniitty, P. Mäki-Arvela, A. Nunes Villela, A. Kalantar Neyestanaki, R. Leino, T. Salmi, R. Sjöholm, E. Laine, J. Väyrynen, T. Ollonqvist, P. J. Kooyman, Catal. Today 2000, 60, 175-184;
46. b) E. Toukoniitty, P. Mäki-Arvela, M. Kuzma, A. Villela, A. Kalantar Neyestanaki, T. Salmi, R. Sjöholm, R. Leino, E. Laine, D. Yu. Murzin, J. Catal. 2001, 204, 281-291;
47. c) E. Toukoniitty, I. Busygin, R. Leino, D. Yu. Murzin, J. Catal. 2004, 227, 210-216;
48. d) E. Toukoniitty, B. Ševčíková, P. Mäki-Arvela, J. Wärnå, T. Salmi, D. Yu. Murzin, J. Catal. 2003, 213, 7-16.
49. a) P. M. Subramanian, S. K. Chatterjee, M. C. Bhatia, J. Chem. Technol. Biotechnol. 1987, 39, 215-218;
50. b) P. Iwan, G. Goetz, S. Schmitz, B. Hauer, M. Breuer, M. Pohl, J. Mol. Catal. B: Enzym. 2001, 11, 387-396.
51. D. Gala, D. J. DiBenedetto, J. E. Clark, B. L. Murphy, D. P. Schumacher, M. Steinman, Tetrahedron Lett. 1996, 37, 611-614.
52. A. Lindholm, P. Mäki-Arvela, E. Toukoniitty, T. A. Pakkanen, J. T. Hirvi, T. Salmi, D. Yu. Murzin, R. Sjöholm, R. Leino, J. Chem. Soc., Perkin Trans. 1 2002, 2605-2612.
53. For a review, see: K. Kacprzak, J. Gawroński, Synthesis 2001, 961-998.
54. a) L. H. Sommer, J. E. Lyons, H. Fujimoto, J. Am. Chem. Soc. 1969, 91, 7051-7061;
55. b) M. A. Brook, Silicon in Organic, Organometallic and Polymer Chemistry, John Wiley & Sons, New York, 2000, p. 409.
56. B. J. Oleksyn, Acta Crystallogr., Sect. B 1982, 38, 1832-1834.
57. a) Y. Orito, S. Imai, S. Niwa, J. Chem. Soc., Jpn. 1979, 8, 1118-1120;
58. b) Y. Orito, S. Imai, S. Niwa, J. Chem. Soc., Jpn. 1980, 2, 670-672;
59. c) Y. Orito, S. Imai, S. Niwa, J. Chem. Soc., Jpn. 1982, 137-138;
60. d) Y. Orito, S. Imai, S. Niwa, G.-H. Nguyen, J. Synth. Org. Chem. Jpn. 1979, 37, 173-174;
61. e) Y. Orito, S. Imai, S. Niwa, 43rd Catalyst Forum, Japan, 1978, p. 30.
62. T. Mallat, Z. Bodnar, B. Minder, K. Borszeky, A. Baiker, J. Catal. 1997, 168, 183-193.
63. a) T. Bürgi, A. Baiker, J. Am. Chem. Soc. 1998, 120, 12920-12926;
64. b) G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. S. Svendsen, I. Marko, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 8069-8076;
65. c) G. D. H. Dijkstra, R. M. Kellogg, H. Wynberg, J. Org. Chem. 1990, 55, 6121-6131.
66. H.-U. Blaser, H. P. Jalett, D. Monti, J. F. Reber, J. T. Wehrli, Stud. Surf. Sci. Catal. 1988, 41, 153-163.
67. E. Toukoniitty, D. Yu. Murzin, Catal. Lett. 2004, 93, 171-176.
68. I. Busygin, E. Toukoniitty, R. Leino, D. Yu. Murzin, J. Mol. Catal., A: Chem. 2005, in press.
69. V. F. Mironov, V. P. Kozyukov, V. D. Sheludyakov, Dokl. Akad. Nauk SSSR 1968, 179, 600-603.
70. L. H. Sommer, C. L. Frye, G. A. Parker, K. W. Michael, J. Am. Chem. Soc. 1964, 86, 3271-3276.
71. R. Laatikainen, M. Niemitz, U. Weber, J. Sundelin, T. Hassinen, J. Vepsäläinen, J. Magn. Reson., Ser. A 1996, 120, 1-10.
72. Z. Otwinowski, W. Minor, in Methods in Enzymology (Eds.: C. W. Carter, R. M. Sweet), Academic Press, London, 1997, vol. 276, part A, p. 307.
73. G. M. Sheldrick, SHELXS97 and SHELXL97, University of Göttingen, Germany, 1997.
74. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.