Structures and reaction pathways in rhodium(I)-catalyzed hydrogenation of enamides: A model DFT study

Journal of the American Chemical Society

Volumn 121, Issue 38, 1999, Pages 8741-8754

  Landis, Clark R ^a   Hilfenhaus, Peter ^a   Feldgus, Steven ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLONITRILE; HYDROGEN; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENERGY; HYDROGENATION; MODEL;

EID: 0033615268     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991606u     Document Type: Article

References (66)

1. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112.
2. Koenig, K. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1985; Vol. 5.
3. Ojima, I. Catalytic Asymmetric Synthesis; VCH: New York, 1993.
4. Noyori, R. Acta Chem. Scand. 1996, 50, 380-390.
5. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518-8519.
6. Burk, M. J.; Gross, M. F.; Harper, T. G. P.; Kalberg, C. S.; Lee, J. R.; Martinez, J. P. Pure Appl. Chem. 1996, 68, 37-44.
7. Ager, D. J.; Fotheringham, I. G.; Laneman, S. A.; Pantaleone, D. P.; Taylor, P. P. Chim. Oggi-Chem. Today 1997, 15, 11-14.
8. Nagel, U.; Albrecht, J. Topics Catal. 1998, 5, 3-23.
9. Kreuzfeld, H. J.; Dobler, C.; Schmidt, U.; Krause, H. W. Chirality 1998, 10, 535-539.
10. Zhu, G. X.; Zhang, X. M. J. Org. Chem. 1998, 63, 3133-3136.
11. Zhu, G. X.; Cao, P.; Jiang, Q. Z.; Zhang, X. M. J. Am. Chem. Soc. 1997, 119, 1799-1800.
12. RajanBabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012-6028.
13. Halpern, J. Science 1982, 217, 401-407.
14. Brown, J. M.; Chaloner, P. A. In Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum: New York, 1983; p 137.
15. Brown, J. M. Chem. Soc. Rev. 1993, 22, 25-41.
16. Boudait, M.; Djegamariadassou, G. Catal. Lett. 1994, 29, 7-13.
17. Heller, D.; Thede, R.; Haberland, D. J. Mol. Catal. A-Chem. 1997, 115, 273-281.
18. Landis, C.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754.
19. Sun, Y. K.; Landau, R. N.; Wang, J.; LeBlond, C.; Blackmond, D. G. J. Am. Chem. Soc. 1996, 118, 1348-1353.
20. Bircher, H.; Bender, B. R.; von Phillipsborn, W. Magn. Reson. Chem. 1993, 31, 293-298.
21. Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952-5954.
22. Brown, J. M.; Chaloner, P. A. J. Chem. Soc., Chem. Commun. 1980, 344-346.
23. Bosnich, B., Ed. Asymmetric Catalysis; Martinus Nijhoff: Dordrecht, 1986; Vol. 103.
24. Brauch, T. W.; Landis, C. R. Inorg. Chim. Acta 1998, 270, 285-297.
25. Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057.
26. Brown, J. M.; Parker, D. Organometallics 1982, 1, 950-956.
27. Koenig, K. E.; Bachman, G. L.; Vineyard, B. D. J. Org. Chem. 1980, 45, 2362-2365.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Kieth, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe. M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision D4; Gaussian, Inc.: Pittsburgh, PA, 1995.
29. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
30. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
31. Schmid, R.; Herrmann, W. A.; Frenking, G. Organometallics 1997, 16, 701-708.
32. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
33. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 285-298.
34. Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, p 1.
35. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-142.
36. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431-1441.
37. Huzinaga, S. Gaussian Basis Sets for Molecular Calculations; Elsevier: Amsterdam, 1984.
38. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
39. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
40. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
41. Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209-214.
42. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163-171.
43. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegman, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111-114.
44. Brown, J. M.; Evans, P. L. Tetrahedron 1988, 44, 4905-4916.
45. Bogdan, P. L.; Irwin, J. J.; Bosnich, B. Organometallics 1989, 8, 1450-1453.
46. Chan, A. S. C.; Pluth, J. J.; Halpern, J. Inorg. Chim. Acta 1979, 37, L477-L479.
47. McCullough, B.; Halpern, J.; Thompson, M. R.; Landis, C. R. Organometallics 1990, 9, 1392-1395.
48. Kless, A.; Borner, A.; Heller, D.; Selke, R. Organometallics 1997, 16, 2096-2100.
49. Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365-374.
50. Koga, N.; Jin, S. Q.; Morokuma, K. J. Am. Chem. Soc. 1988, 110, 3417-3425.
51. (51 ) Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper & Row: New York, 1981.
52. Sargent, A. L.; Hall, M. B.; Guest, M. F. J. Am. Chem. Soc. 1992, 114, 517-522.
53. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334-338.
54. Berry, R. S. J. Chem. Phys. 1960, 32, 933-938.
55. Bailar, J. C. J. Inorg. Nucl. Chem. 1958, 8, 165-175.
56. Abu-Hasanayn, F.; Krogh-Jespersen, K.; Goldman, A. S. J. Am. Chem. Soc. 1993, 115, 8019-8023.
57. Halpern, J.; Okrasinski, S. J. Unpublished results, 1981.
58. Halpern, J.; Riley, D. P.; Chan, A. S. C.; Pluth, J. J. J. Am. Chem. Soc. 1977, 99, 8055-8057.
59. Brown, J. M.; Canning, L. R.; Downs, A. R., Forster, A. M. J. Organomet. Chem. 1983, 255, 103-111.
60. Halpern, J.; Landis, C. R. Unpublished results, 1983.
61. Harthun, A.; Kadyrov, R.; Selke, R.; Bargon, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1103-1005.
62. Brown, J. M.; Maddox, P. J. J. Chem. Soc., Chem. Commun. 1987, 1276-1278.
63. Chan, A. S. C.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 838-840.
64. Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034.
65. Leitner, W.; Brown, J. M.; Brunner, H. J. Am. Chem. Soc. 1993, 115, 152-159.
66. We note that turnover-limiting alkene insertion may help to explain Brown and Leitner's observation that enamide reduction with formic acid yields enantioselectivities that are nearly identical to those obtained by reduction with dihydrogen, even though dihydrogen is not an intermediate in the formic acid reductions.