A generalized two-point H-bonding model for catalytic stereoselective hydrogenation of activated ketones on chirally modified platinum

Journal of the American Chemical Society

Volumn 128, Issue 23, 2006, Pages 7588-7593

  Lavoie, Stéphane ^a   Laliberté, Marc André ^a   Temprano, Israel ^a   McBreen, Peter H ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ESTERS; HYDROGEN BONDS; HYDROGENATION; MATHEMATICAL MODELS; PLATINUM;

H-BONDING MODEL; MECHANISTIC MODELS; ORITO REACTION; RACEMIC REACTION;

KETONES;

AROMATIC COMPOUND; CARBONYL DERIVATIVE; ESTER DERIVATIVE; KETONE; PLATINUM;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; HYDROGEN BOND; HYDROGENATION; MOLECULAR INTERACTION; MOLECULAR MODEL; POLARIZATION; RACEMIC MIXTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 33745078415     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060504i     Document Type: Article

References (56)

1. Trost, B. M. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5348-5355.
2. (a) Davis, M. E. Top. Catal. 2003, 25, 3-7.
3. (b) Stacchiola, D.; Burkholder, L.; Zheng, T.; Weinert, M.; Tysoe, W. T. J. Phys. Chem. B 2005, 109, 851.
4. (c) Humblot, V.; Haq, S.; Muryn, C.; Hoter, W. A.; Raval, R. J. Am. Chem. Soc. 2002, 124, 503-510.
5. (d) Bonello, J. M.; Williams, F. J.; Lambert, R. M. J. Am. Chem. Soc. 2003, 125, 2723-2729.
6. (e) Ma, J.; Lee, I.; Kubota, J.; Zaera, F. J. Mol. Catal. A: Chem. 2004, 216, 199-207.
7. (f) Scholl, D. S. Langmuir 1998, 14, 862-867.
8. (g) Horvath, J. D.; Gellman, A. J. J. Am. Chem. Soc. 2002, 124, 2384-2392.
9. (h) Baddeley, C. J. Top. Catal. 2003, 25, 17-28.
10. Orito, Y.; Imai, S.; Niwa, S. J. Chem. Soc. Jpn. 1979, 8, 1118-1120.
11. (a) Burgï, T.; Baiker, A. Acc. Chem. Res. 2004, 37, 909-917.
12. (b) Vargas, A.; Burgi, T.; Baiker, A. J. Catal. 2004, 226, 69-82.
13. (a) Exner, C.; Pfaltz, A.; Studer, M.; Blaser, H.-U. Adv. Synth. Catal. 2003, 345, 1253-1260.
14. (b) Blaser, H. U.; Jalett, H. P.; Lottenbach, W.; Studer, M. J. Am. Chem. Soc. 2000, 122, 12682-12682.
15. Studer, M.; Blaser, H.-U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45-65.
16. von Arx, M.; Mallat, T.; Baiker, A. Top. Catal. 2002, 19, 75-87.
17. (a) Wells, P. B.; Wilkinson, A. G. Top. Catal. 1998, 5, 39-50.
18. (b) Simons, K. E.; Maheux, P. A.; Griffiths, S. P.; Sutherland, L. M.; Johnston, P.; Wells, P. B.; Carley, A. F.; Rajumon, M. K.; Roberts, M. W.; Ibbotson, A. Recl. Trav. Chim. Pays-Bas 1994, 113, 465-474.
19. Vayner, G.; Houk, K. N.; Sun, Y.-K. J. Am. Chem. Soc. 2004, 126, 199-203.
20. Jenkins, D. J.; Alabdulrahman, A. M. S.; Attard, G. A.; Griffin, K. G.; Johnston, P.; Wells, P. B. J. Catal. 2005, 234, 230-239.
21. Bartok, M.; Felfoldi, K.; Torok, B.; Bartok, T. Chem. Commun. 1998, 2605-2606.
22. (a) Lavoie, S.; Laliberté, M.-A.; McBreen, P. H. J. Am. Chem. Soc. 2003, 125, 15756-15757.
23. (b) Lavoie, S.; Laliberté, M.-A.; McBreen, P. H. Catal. Lett. 2004, 97, 111-114.
24. (c) Lavoie, S.; McBreen, P. H. J. Phys. Chem. B 2005, 109, 11986-11990.
25. (a) Diezi, S.; Mallat, T.; Szabo, A.; Baiker, A. J. Catal. 2004, 228, 162-173.
26. (b) Bonalumi, N.; Vargas, A.; Feri, D.; Burgi, T.; Mallat, T.; Baiker, A. J. Am. Chem. Soc. 2005, 127, 8467-8477.
27. (c) Cserenyi, S.; Felfeldi, K.; Balazsik, K.; Szollosi, G.; Bucsi, I.; Bartok, M. J. Mol. Catal. A: Chem. 2005, 247, 108.
28. Orglmeister, E.; Mallat, T.; Baiker, A. Adv. Synth. Catal. 2005, 347, 78-86.
29. Marinas, A.; Mallat, T.; Baiker, A. J. Catal. 2004, 221, 666-669.
30. Bonalumi, N.; Bürgi, T.; Baiker, A. J. Am. Chem. Soc. 2003, 125, 13342-13343.
31. Vargas, A.; Ferri, D.; Baiker, A. J. Catal. 2005, 236, 1-8.
32. Evans, T.; Woodhead, A. P.; Gutiérrez-Sosa, A.; Thornton, G.; Hall, T. J.; Davis, A. A.; Young, N. A.; Wells, P. B.; Oldman, R. J.; Plashkevych, O.; Vahtras, O.; Ågrend, H.; Carravetta, V. Surf. Sci. 1999, 436, L691-L696.
33. (a) LeBlanc, R. J.; Chu, W.; Williams, C. T. J. Mol. Catal. A: Chem. 2004, 212, 277-289.
34. (b) Kubota, J.; Ma, Z.; Zaera, F. Langmuir 2003, 19, 3371.
35. (c) Chu, W.; LeBlanc, R. J.; Williams, C. T.; Kubota, J.; Zaera, F. J. Phys. Chem. B 2003, 107, 14365.
36. (d) Ferri, D.; Burgi, T.; Baiker, A. Chem. Commun. 2001, 1172.
37. (e) Ferri, D.; Burgi, T. J. Am. Chem. Soc. 2001, 123, 12074-12084.
38. Toukoniitty, E.; Nieminen, V.; Taskinen, A.; Päivärinta, J.; Hotokka, M.; Murzin, D. Y. J. Catal. 2004, 224, 326-339.
39. Taskinen, A.; Nieminen, V.; Toukoniitty, E.; Y., M. D.; Hotokka, M. Tetrahedron 2005, 61, 8109-8119.
40. (a) Venkatesan, V.; Fujii, A.; Ebata, T.; Mikami, N. Chem. Phys. Lett. 2004, 394, 45-48.
41. (b) Venkatesan, V.; Fujii, A.; Mikami, N. Chem. Phys. Lett. 2005, 409, 57-62.
42. (c) Venkatesan, V.; Fujii, A.; Ebata, T.; Mikami, N. J. Phys. Chem. A 2005, 109, 915-921.
43. (a) Bryantsev, V. S.; Hay, B. P. J. Am. Chem. Soc. 2005, 127, 8282-8283.
44. (b) Bryantsev, V. S.; Hay, B. P. Org. Lett. 2005, 7, 5031-5034.
45. (a) Gao, S. W.; Hahn, J. R.; Ho, W. J. Chem. Phys. 2003, 119, 6232-6236.
46. (b) Hahn, J. R.; Ho, W. J. Phys. Chem. B 2005, 109, 20350-20354.
47. (a) Morin, C.; Simon, D.; Sautet, P. J. Phys. Chem. B 2004, 108, 12084-12091.
48. (b) Tan, Y. P.; Khatua, S.; Jenkins, S. J.; Yu, J.-Q.; Spencer, J. B.; King, D. A. Surf. Sci. 2005, 589, 173-183.
49. (a) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062-2064.
50. (b) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
51. Sola, J.; Riera, A.; Verdeguer, X.; Maestro, M. A. J. Am. Chem. Soc. 2005, 117, 13629-1363.
52. Loffreda, D.; Delbecq, F.; Viene, F; Sautet, P. J. Am. Chem. Soc. 2006, 128, 1316-1323.
53. Wells, P. B.; Wells, P. K. Chiral Catalyst Immobilization and Recycling. Wiley-VCH: Weinheim, Toronto, 2000.
54. von Arx, M.; Dummer, N.; Willcock, D. J.; Taylor, S. H.; Wells, R. P. K.; Wells, P. B.; Hutchings, G. J. Chem. Commun. 2003, 1926-1927.
55. Ma, Z.; Zaera, F. J. Mol. Catal. A: Chem. 2004, 216, 199-207.
56. de Vos, D. E.; Bruyn, M. D.; Parvulescu, V. I.; Coca, F. G.; Jacobs, P. A. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, Toronto, 2000.