Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones

Journal of Organic Chemistry

Volumn 69, Issue 15, 2004, Pages 4885-4890

  Brandt, Peter ^a   Roth, Peter ^b   Andersson, Pher G ^b  

^a BIOVITRUM AB   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ELECTROSTATICS; HYDROGENATION; PROBABILITY DENSITY FUNCTION; RUTHENIUM COMPOUNDS; SOLVENTS;

CATALYTIC SYSTEMS; DENSITY FUNCTIONAL THEORY; ELECTROSTATIC EFFECTS; ENANTIOSELECTIVITY;

KETONES;

ALKYL GROUP; AMINE; AMINOALCOHOL; KETONE; LIGAND; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DENSITY FUNCTIONAL THEORY; DISPERSION; ELECTRICITY; ENANTIOSELECTIVITY; FORCE; HYDROGENATION; MOLECULAR INTERACTION; PHASE TRANSITION; REDUCTION; SOLVENT EFFECT; STEREOCHEMISTRY;

EID: 3543040636     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030378q     Document Type: Article

References (64)

1. Reviews: (a) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
2. (b) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
3. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
4. (b) Takerhara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. Chem. Commun. 1996, 233.
5. (c) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
6. (a) Nordin, S. J. M.; Roth, P.; Tarnai, T.; Alonso, D. A.; Brandt, P.; Andersson, P. G. Chem. Eur. J. 2001, 7, 1431.
7. (b) Alonso, D. A.; Nordin, S. J. M.; Roth, P.; Tarnai, T.; Thommen, M.; Pittelkow, U.; Andersson, P. G. J. Org. Chem. 2000, 65, 3116.
8. (c) Alonso, D. A.; Guijarro, D.; Pinho, P.; Temme, O.; Andersson, P. G. J. Org. Chem. 1998, 63, 2749.
9. Palmer, M. J.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226.
10. Petra, D. G. I.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; van Loon, A. M.; de Vries, J. G.; Schoemaker, H. E. Eur. J. Inorg. Chem. 1999, 2335.
11. Schwink, L.; Ireland, T.; Puntener, K.; Knochel, P. Tetrahedron: Asymmetry 1998, 9, 1143.
12. (a) Frost, C. G.; Mendoca, P. Tetrahedron: Asymmetry 2000, 11, 1845.
13. (b) Henning, M.; Puntener, K.; Scalone, M. Tetrahedron: Asymmetry 2000, 11, 1849.
14. (c) Ohta, T.; Nakahara, S.; Shigemura, Y.; Hattori, K.; Furukawa, I. Appl. Organomet. Chem. 2001, 15, 699.
15. (d) Aitali, M.; Allaoud, S.; Karim, A.; Meliet, C.; Mortreaux, A. Tetrahedron: Asymmetry 2000, 11, 1367.
16. (e) Rhyoo, H. Y.; Yoon, Y.-A.; Park, H.-J.; Chung, Y. K. Tetrahedron Lett. 2001, 45, 5045.
17. (f) Faller, J. W.; Lavoie, A. R. Organometallics 2001, 20, 5245.
18. (g) Brunner, H.; Henning, F.; Weber, M. Tetrahedron: Asymmetry, 2001, 13, 37.
19. (h) Everaere, K.; Mortreux, M.; Bulliard, A.; Brusse, J.; van der Gen, A.; Nowogrocki, G.; Carpentier, J.-F. Eur. J. Org. Chem. 2001, 275.
20. Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.
21. Yamakawa, M.; Ito, H.; Noyori, R. J. Am. Chem. Soc. 2000, 122, 1466.
22. Petra, D. G. I.; Reek, J. N. H.; Handgraaf, J.-W.; Meijer, E. J.; Dierkes, P.; Kamer, P. C.; Brusse, J.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. Chem. Eur. J. 2000, 6, 2818.
23. (a) Haack, K.-A.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
24. (b) Kenny, J. A.; Versluis, K.; Heck, A. J. R.; Walsgrove, T.; Wills, M. Chem. Commun. 2000, 199.
25. Casey, C. P.; Johnson J. B. J. Org. Chem. 2003, 68, 1998. Nordin, S. J. M.; Andersson, P. G.; Ryberg, P. Manuscript in preparation. Casey, C. P.; Johnson J. B. J. Org. Chem. 2003, 68, 1998.
26. Casey, C. P.; Johnson J. B. J. Org. Chem. 2003, 68, 1998. Nordin, S. J. M.; Andersson, P. G.; Ryberg, P. Manuscript in preparation. Casey, C. P.; Johnson J. B. J. Org. Chem. 2003, 68, 1998.
27. Casey, C. P.; Johnson J. B. J. Org. Chem. 2003, 68, 1998. Nordin, S. J. M.; Andersson, P. G.; Ryberg, P. Manuscript in preparation. Casey, C. P.; Johnson J. B. J. Org. Chem. 2003, 68, 1998.
28. (a) Silverman, R. B. In The Organic Chemistry of Enzyme-Catalyzed Reaction; Academic Press: San Diego, 2000.
29. (b) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 707.
30. Kolb, H. C.; Andersson, P. G.; Bennani, Y. L.; Crispino, G. A.; Jeong, K. S.; Kwong, H. L.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 12226.
31. (b) Norrby, P.-O.; Kolb, H. C.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 8470.
32. (c) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1998, 118, 319.
33. (d) Ujaque, G.; Maseras, F.; Lledos, A. J. Am. Chem. Soc. 1999, 121, 1317.
34. (e) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156.
35. (f) For a review, see: Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
36. (g) For a detailed analysis of the selectivity in the reaction, see: Norrby, P.-O.; Rasmussen, T.; Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 10186.
37. (a) Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768.
38. (b) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 720, 11192.
39. (c) Nakamura, K.; Houk, K. N. Org. Lett. 1999, 1, 2049.
40. (d) Martin, C. B.; Mulla, H. R.; Willis, P. G.; Cammers-Goodwin, A. J. Org. Chem. 1999, 64, 7802.
41. (e) Müller-Dethlefs, K.; Hobza, P. Chem. Rev. 2000, 100, 143.
42. (f) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651.
43. (g) Ribas, J.; Cubero, E.; Luque, F. J.; Orozco, M. J. Org. Chem. 2002, 67, 7057.
44. (h) Meyer, E. A.; Castellano, R. K.; Diedriech, F. Angew. Chem., Int. Ed. 2003, 42, 1210.
45. (i) Hunter, C. A.; Low, C. M. R.; Vinter, J. G.; Zonta, C. J. Am. Chem. Soc. 2003, 725, 9936.
46. Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem., Int. Ed. 2001, 40, 2818.
47. (a) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1986, 255, 327.
48. (b) For a review, see also: Tomasi, J.; Persisco, M. Chem. Rev. 1994, 94, 2027.
49. 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.3; Gaussian, Inc.: Pittsburgh, PA, 1998.
50. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
51. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
52. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
53. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1980, 11, 361.
54. Jaguar 4.2; Schrödinger, Inc., Portland, OR, 1991-2000.
55. (a) Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. 1996, 100, 18790.
56. (b) Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104.
57. More elaborate methods such as cross validated partial least squares (PLS) using the individual electrostatic potential fitted atomic charges gave improved results. However, as the purpose of this study is to illustrate the relative contribution of different forces rather than developing predictive models, we did not include these models.
58. Charge transfer is also included but not likely to be of importance for these systems.
59. For use of STERIMOL parameters in QSAR, see: Högberg, T.; Norinder, U. In A Textbook of Drug Design and Development, 2nd ed.; Krogsgaard-Larsen, P.; Liljefors, T.; Madsen, U., Eds.; Harwood Academic Publichers, Amsterdam, 1996.
60. Bennet, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233.
61. (a) Doucet, H.; Fernandez, E.; Layzell, T. P.; Brown, J. M. Chem. Eur. J. 1999, 5, 1320.
62. (b) Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957.
63. (c) Blake, A. J.; Cunningham, A.; Ford, A.; Teat, S. J.; Woodward, S. Chem. Eur. J. 2000, 6, 3586.
64. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.