Origins of Enantioselectivity in Reductions of Ketones on Cinchona Alkaloid Modified Platinum

Journal of the American Chemical Society

Volumn 126, Issue 1, 2004, Pages 199-203

  Vayner, Grigoriy ^a   Houk, K N ^a   Sun, Y K ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; CATALYSIS; HYDROGENATION; PLATINUM; PROBABILITY DENSITY FUNCTION; STEREOCHEMISTRY;

STEREOSELECTIVITY;

KETONES;

AMPHOLYTE; CARBONYL DERIVATIVE; CINCHONA ALKALOID; KETONE; PLATINUM DERIVATIVE; QUINOLINE DERIVATIVE;

ADSORPTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; FORCE; FORCE FIELD METHOD; HYDROGENATION; MODEL; REDUCTION; STEREOCHEMISTRY;

EID: 0345868508     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035147f     Document Type: Article

References (47)

1. (a) Studer, M.; Blaser, H.-U.; Exner, Y. Adv. Synth. Catal. 2003, 345, 45.
2. (b) Blaser, H.-U.; Jalett, H. P.; Lottenbach, W.; Studer, M. J. Am. Chem. Soc., 2000, 122, 12675.
3. (c) Baiker, A.; Blaser, H.-U. In Handbook of Heterogeneous Catalysis; Ertl, G., Knozinger, H., Weitkamp, J., Eds.; VCH: Weinheim, 1997; Vol. 4, p 2422.
4. (d) Torok, B.; Felfoldi, K.; Balazsik, K.; Bartok, M Chem. Commun. 1999, 1725-5.
5. Orito, Y.; Imai, S.; Nguyen, G. Synth. Org. Chem. Jpn. 1979, 37, 173.
6. (a) von Arx, M.; Mallat, T.; Baiker, A. Tetrahedron: Asymmetry, 2001, 12, 3089-94.
7. (b) Bürgi, T.; Baiker, A. J. Catal. 2000, 194, 445.
8. (a) Bartok, M.; Felföldi, K.; Török, B.; Bartok, T. Chem. Commun. 1998. 2605-6.
9. (b) Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473 and references therein.
10. Margitfalvi, J. L.; Talas, E.; Tfirst, E.; Kumar, C. V.; Gergely, A. Appl. Catal. A 2000, 191, 177-91.
11. (a) Bartók, M.; Török, B.; Balazsik, K.; Bartók, T. Catal. Lett. 2001, 73, 127.
12. (b) Szöllösi, G.; Felföldi, K.; Bartók, T.; Bartók, M. React. Kinet. Catal. Lett. 2000, 71, 99.
13. (c) Wells, P. B.; Wells, R. P. K. In Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, 2000; p 123.
14. (d) Baiker, A. In Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, 2000; p 155.
15. Augustine, R. L.; Taneilyan, S. K.; Doyle, L. K. Tetrahedron: Asymmetry 1993, 4, 1803-1827.
16. Bartok, M.; Sutyinszki, M.; Felfoldi, K.; Szollosi, Gy. Chem. Commun. 2002, 1130.
17. Sugi Y.; Mitsui S. Tetrahedron 1973, 29, 2041.
18. Phillips, A. P. J. Am. Chem. Soc. 1954, 76, 2211.
19. Schilling, M. L. M.; Roth, H. D.; Herndon W. C. J. Am. Chem. Soc. 1980, 102, 4271-2
20. Calter, M. A. J. Org. Chem. 1996, 61, 8006-7.
21. Spivey, A. C.; Andrews B. I. Angew. Chem., Int. Ed. 2001, 40, 3131-4.
22. Margitfalvi, J. L.; Hegedus, M. J. Mol. Catal. A. 1996, 107, 281.
23. (a) von Arx, M.; Bürgi, T.; Mallat, T.; Baiker, A. Chem. Eur. J. 2002, 8, 1430.
24. (b) Török, B.; Balazsik, K.; Felföldi, K.; Bartók, M. Stud. Surf. Sci. Catal. 2000, 130, 3381.
25. Powers, J. C.; Westheimer, F. H. J. Am. Chem. Soc. 1960, 82, 5431. Cordes, E. H.; Jencks, W. P. J. Am. Chem. Soc. 1963, 85, 2843.
26. Powers, J. C.; Westheimer, F. H. J. Am. Chem. Soc. 1960, 82, 5431. Cordes, E. H.; Jencks, W. P. J. Am. Chem. Soc. 1963, 85, 2843.
27. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
28. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230.
31. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230.
32. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrikson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
33. Bürgi, T.; Baiker, A. J. Am. Chem. Soc. 1998, 120, 12920-6.
34. 19
35. Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
36. Cannizzaro, C. E.; Houk, K. N. J. Am. Chem. Soc. 2002, 124, 7163.
37. For discussions on the relative position of the quinoline ring on Pt surface, see ref 15 and: (a) Kubota, J.; Zaera, F. J. Am. Chem. Soc. 2001, 123, 11115.
38. (b) Ferri, D.; Burgi, T. J. Am. Chem. Soc. 2001, 123, 12074.
39. (c) Chu, W.; LeBlanc, R. J.; Williams, C. T. Catal. Commun. 2002, 3, 547.
40. (d) Evans, T.; Woodhead, A. P.; Gutierrez-Sosa, A.; Thornton, G.; Hall, T. J.; Davis, A. A.; Young, N. A.; Wells, P. B.; Oldman R. J.; Plashkevych, O.; Vahtras, O.; Agren, H.; Carravetta, V. Surf. Sci. 1999, 436, L691.
41. Thiel, P. A.; Madey, T. E. Surf. Sci. Rep. 1987, 7, 211.
42. This has been found by XANES studies (see Burgi, T.; Atamny, F.; Knop-Gericke, A.; Havecker, M.; Schedel-Niedrig, T.; Schlogl, R.; Baiker, A. Catalysis Lett. 2000, 66, 109-12.) The orientation of pyruvate was found to change in the presence of hydrogen.
43. Halpern, J. Science 1982, 217, 401-7.
44. Blaser, H.-U.; Jalett, H.-P.; Garland, M.; Studer, M.; Thies, H.; Wirth-Tijani, A. J. Catal. 1998, 173, 282-294.
45. Bartok, M.; Balazsik, K.; Szollosi, Gy.; Bartok, T. J. Catal. 2002, 205, 168.
46. The geometries shown in Figure 9 were obtained with MacroModel. Pt atoms were frozen during all calculations, with a Pt-Pt distance of 2.775 Å. Pt-O distances were constrained to 2.1 A. Everything else was allowed to relax. The resulting structures automatically converge to geometries shown in Figure 9.
47. LeBlond, C.; Wang, J.; Liu, J.; Andrews, A. T.; Sun Y.-K. J. Am. Chem. Soc. 1999, 121, 4920-1.