Solvent effects in enantioselective hydrogenation of 1-phenyl-1,2-propanedione

Journal of Molecular Catalysis A: Chemical

Volumn 192, Issue 1-2, 2003, Pages 135-151

  Toukoniitty, E ^a   Maiki Arvela P ^a   Kuusisto, J ^a   Nieminen, V ^a   Paivarinta J ^b   Hotokka, M ^b   Salmi, T ^a   Murzin, D Yu ^a  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b ÅBO AKADEMI UNIVERSITY   (Finland)

Author keywords

Dielectric constant; Diones; Enantioselective hydrogenation; Pt catalyst; Solvent effect; Transition state theory

Indexed keywords

HYDROGENATION; METHANOL; SOLVENTS; TOLUENE;

LIQUID PHASE;

CATALYSTS;

1 PHENYL 1,2 PROPANEDIONE; CINCHONIDINE; PROPANE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; DIELECTRIC CONSTANT; ENANTIOSELECTIVITY; HYDROGENATION; QUANTUM CHEMISTRY; QUANTUM THEORY; SOLID STATE; SOLUBILITY; THEORY;

EID: 0347295968     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(02)00415-6     Document Type: Article

References (49)

1. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim, 1990.
2. L. Červený, V. Růžička, Adv. Catal. 30 (1981) 335.
3. P.G.J. Koopman, H.M.A. Buurmans, A.P.G. Kieboom, H. van Bekkum, Recueil, J. R. Netherlands Chem. Soc. 100 (1981) 156.
4. H.-U. Blaser, H.-P. Jalett, M. Müller, M. Studer, Catal. Today 37 (1997) 441.
5. A. Baiker, J. Mol. Catal. A: Chem. 115 (1997) 473.
6. A. Baiker, J. Mol. Catal. A: Chem. 163 (2000) 205.
7. C. LeBlond, J. Wang, A.T. Andrews, Y.-K. Sun, Topics Catal. 13 (2000) 169.
8. J. Wehrli, A. Baiker, H.-U. Monti, H. Jalett, J. Mol. Catal. 57 (1989) 245.
9. H.-U. Blaser, H. Jalett, J. Wiehl, J. Mol. Catal. 68 (1991) 215.
10. T. Bürgi, A. Baiker, J. Am. Chem. Soc. 120 (1998) 12920.
11. L. Onsager, J. Am. Chem. Soc. 58 (1936) 1486.
12. 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. 204 (2001) 281.
13. V.B. Shukala, P.R. Kulkami, World J. Microbiol. Biotechnol. 16 (2000) 499.
14. E. Toukoniitty, P. Mäki-Arvela, A. Kalantar Neyestanaki, T. Salmi, R. Sjöholm, R. Leino, E. Laine, P.J. Kooyman, T. Ollonqvist, J. Väyrynen, Appl. Catal. A: Gen. 216 (2001) 73.
15. E. Toukoniitty, P. Mäki-Arvela, A. Villela, A. Kalantar Neyestanaki, T. Salmi, R. Leino, R. Sjöholm, E. Laine, J. Väyrynen, J. Ollonqvist, P.J. Kooyman, Catal. Today 60 (2000) 175.
16. E. Toukoniitty, P. Mäki-Arvela, J. Wärnå, T. Salmi, Catal. Today 66 (2001) 411.
17. H.-U. Blaser, H. Jalett, D. Monti, A. Baiker, J. Wehrli, in: R. Grasselli, A. Sleight (Eds.), Structure-Activity and Selectivity Relationship in Heterogeneous Catalysis, Elsevier, Amsterdam, 1991, p. 147.
18. R. Ditchfield, W.J. Hehre, J.A. Pople, J. Chem. Phys. 54 (2) (1971) 724.
19. W.J. Hehre, R. Ditchfield, J.A. Pople, J. Chem. Phys. 56 (5) (1972) 2257.
20. T. Clark, J. Chandrasekhar, G.W. Spitznagel, P.V.R. Schleyer, J. Comput. Chem. 4 (3) (1983) 294.
21. P.C. Hariharan, J.A. Pople, Theor. Chim. Acta 28 (3) (1973) 213.
22. S. Miertus, J. Tomasi, Chem. Phys. 65 (1982) 239.
23. P.J. Stephens, F.J. Devlin, C.S. Ashvar, C.F. Chabalowski, M.J. Frisch, Faraday Discuss. 99 (1994) 103.
24. A.D. Becke, J. Chem. Phys. 98 (1993) 5648.
25. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785.
26. Gaussian 98, Revision A.7, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian Inc., Pittsburgh, PA, 1998.
27. E. Toukoniitty, P. Mäki-Arvela, N. Kumar, T. Salmi, D. Yu. Murzin, Influence of mass transfer effects on regio- and enantioselectivity in hydrogenation of 1-phenyl-1,2-propanedione over Pt modified catalysts, submitted for publication.
28. E. Toukoniitty, B. Ševčíková, P. Mäki-Arvela, J. Wärnå, T. Salmi, D. Yu. Murzin, Kinetics and modeling of hydrogenation of 1-phenyl-1,2-propanedione: coverage dependent adsorption modes of substrate and catalyst modifier, submitted for publication.
29. M. Schürch, O. Schwalm, T. Mallat, J. Weber, A. Baiker, J. Catal. 169 (1997) 275.
30. J. Slipszenko, S. Griffiths, P. Johnston, K. Simons, W. Vermeer, P. Wells, J. Catal. 179 (1998) 267.
31. M. Studer, V. Okafor, H.-U. Blaser, J. Chem. Soc. Chem. Commun. (1998) 1053.
32. E. Toukoniitty, P. Mäki-Arvela, V. Nieminen, M. Hotokka, J. Päivärinta, T. Salmi, D. Yu. Murzin, Enhanced regioselectivity in batch and continuous hydrogenation of 1-phenyl-1,2-propanedione over modified Pt catalysts, submitted for publication.
33. R.L. Augustine, P. Techasauvapak, J. Mol. Catal. 87 (1994) 95 (and reference therein).
34. B.A. Sexton, A.E. Hughes, Surf. Sci. 140 (1984) 227.
35. R. Augustine, R. Warner, M. Melnick, J. Org. Chem. 49 (1984) 4853.
36. J.P. Wauquier, J.C. Jungers, Bull. Soc. Chim. Fr. (1957) 1280.
37. H.-U. Blaser, H. Jalett, D. Monti, J. Reber, J. Wehrli, in: M. Guisnet, et al. (Eds.), Heterogeneous Catalysis and Fine Chemicals, Elsevier, Netherlands, 1988, p. 153.
38. G.D.H. Dijkstra, R.M. Kellogg, H. Wynberg, J.S. Svendsen, I. Marko, K.B. Sharpless, J. Am. Chem. Soc. 111 (1989) 8069.
39. G.D.H. Dijkstra, R.M. Kellogg, H. Wynberg, J. Org. Chem. 55 (1990) 6121.
40. T. Bürgi, A. Baiker, J. Catal. 194 (2000) 445.
41. M. Bartok, K. Felföldi, G. Szöllosi, T. Bartok, Catal. Lett 61 (1999) 1.
42. D. Ferri, T. Bürgi, A. Baiker, J. Chem. Soc. Perkin Trans. 2 (2) (2000) 221.
43. Y. Orito, S. Imai, S. Niwa, J. Chem. Soc. Jpn. (1980) 670.
44. X. Zuo, H. Liu, J. Tian, J. Mol. Catal. A: Chem. 157 (2000) 217.
45. K.J. Laidler, Chemical Kinetics, Harper & Row, New York, 1987.
46. J.L. Margitfalvi, E. Talas, M. Hegedus, Chem. Commun. (1999) 645.
47. H.-U. Blaser, H.P. Jalett, Stud. Surf. Sci. Catal. 78 (1993) 139.
48. B. Minder, T. Mallat, P. Skrabal, A. Baiker, Catal. Lett. 29 (1994) 115.
49. M. von Arx, T. Mallat, A- Baiker, J. Catal. 202 (2001) 169.