Mechanistic investigations of an enantioselective hydrogenation catalyzed by a ruthenium-BINAP complex. 1. Stoichiometric and catalytic labeling studies

Organometallics

Volumn 17, Issue 11, 1998, Pages 2228-2240

  Wiles, Jason A ^a   Bergens, Steven H ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000514234     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980113f     Document Type: Article

References (57)

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12. For representative examples of mechanistic investigations of hydrogenations catalyzed by ruthenium-BINAP complexes, see: (a) Chan, A. S. C.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95-100. (b) Brown, J. M.; Rose, M.; Knight, F. I.; Wienand, A. Recl. Trav. Chim. Pays-Bas 1995, 114, 242-251. (c) Brown, J. M. Chem. Soc. Rev. 1993, 25-41. (d) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571-1575.
13. For representative examples of mechanistic investigations of hydrogenations catalyzed by ruthenium-BINAP complexes, see: (a) Chan, A. S. C.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95-100. (b) Brown, J. M.; Rose, M.; Knight, F. I.; Wienand, A. Recl. Trav. Chim. Pays-Bas 1995, 114, 242-251. (c) Brown, J. M. Chem. Soc. Rev. 1993, 25-41. (d) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571-1575.
14. For representative examples of mechanistic investigations of hydrogenations catalyzed by ruthenium-BINAP complexes, see: (a) Chan, A. S. C.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95-100. (b) Brown, J. M.; Rose, M.; Knight, F. I.; Wienand, A. Recl. Trav. Chim. Pays-Bas 1995, 114, 242-251. (c) Brown, J. M. Chem. Soc. Rev. 1993, 25-41. (d) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571-1575.
15. For representative examples of mechanistic investigations of hydrogenations catalyzed by ruthenium-BINAP complexes, see: (a) Chan, A. S. C.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95-100. (b) Brown, J. M.; Rose, M.; Knight, F. I.; Wienand, A. Recl. Trav. Chim. Pays-Bas 1995, 114, 242-251. (c) Brown, J. M. Chem. Soc. Rev. 1993, 25-41. (d) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571-1575.
16. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
17. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
18. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
19. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
20. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
21. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
22. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
23. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
24. The mechanism of the enantioselective hydrogenation of (Z)-MAC catalyzed by rhodium-bis(phosphine) complexes is well documented: (a) Giovannetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040-4057. (b) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754. (c) Brown, J. M.; Chaloner, P. A.; Morris, G. A. J. Chem. Soc., Perkin Trans. 2 1987, 1583-1588. (d) Halpern, J. Science 1982, 217, 401-407. (e) Brown, J. M.; Chaloner, P. A. J. Am. Chem. Soc. 1980, 102, 3040-3048. For enantioselective reductions of α-aminoacrylic acid derivatives by dideuterium gas catalyzed by rhodium-bis(phosphine) complexes, see: (f) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138. (g) Scott, J. W.; Keith, D. D.; Nix, G., Jr.; Parrish, D. R.; Remington, S.; Roth, G. P.; Townsend, J. M.; Valentine, D., Jr.; Yang, R. J. Org. Chem. 1981, 46, 5086-5093. (h) Detellier, C.; Gelbard, G.; Kagan, H. B. J. Am. Chem. Soc. 1978, 100, 7556-7561. (i) Koenig, K. E.; Knowles, W. S. J. Am. Chem. Soc. 1978, 100, 7561-7564.
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31. Complex 2 is a well-defined catalyst system for a variety of transformations, including the hydroge;nation of olefins. Wiles, J. A.; Lee, C. E.; McDonald, R.; Bergens, S. H. Organometallics 1996, 15, 3782-3784.
32. 2) = 4 atm.
33. All reactions were carried out under reaction-rate-limiting conditions to eliminate gas-liquid mass transfer effects. For a study describing gas-liquid mass transfer effects on enantioselectivity, see: Sun, Y.; Landau, R. N.; Wang, J.; LeBlond, C.; Blackmond, D. G. J. Am. Chem. Soc. 1996, 118, 1348-1353.
34. The differences between the conditions under which the spectrum was recorded and the optimum conditions for the catalytic hydrogenation resulted from the technical difficulties in carrying out such a reaction in our NMR tubes.
35. Cα)-1. We have been unable to assign other signals to this species.
36. 6-arene ligands.
37. 2.
38. Joshi, A. M.; James, B. R. Organometallics 1990, 9, 199-205.
39. Cα)-1 was observed at room temperature.
40. 2H NMR spectra to those of N-acetylphenylalanine. See ref 3h and the Experimental Section for details.
41. 2 and dideuterium gas. We believe that deuteration at nitrogen is a side reaction which is not part of the mechanism of hydrogenation of (Z)-MAC catalyzed by 2.
42. An NMR tube containing a -80°C argon-saturated acetone solution of 2 was quickly ejected from a cooled (-80°C) NMR probe, injected with an excess of dideuterium gas through a rubber septum, shaken for ∼15 s, and quickly returned to the probe. NMR spectra recorded at -80°C indicated 2-d was the only ruthenium species formed in solution, with concomitant formation of HD gas.
43. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
44. 1 would depend on the enantioselectivity of the catalyst toward (E)-MAC.
45. (a) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2121-2128.
46. (b) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2128-2135.
47. 2 in the reactor and because the concentration of 2 relative to 2-d is probably quite low.
48. Another possibility, which we do not rule out, is that the intrinsic face selectivity of the hydrogenation toward (E)-MAC and (Z)-MAC are the same.
49. (a) Crabtree, R. H.; Quirk, J. M.; Fillebeen-Khan, T.; Morris, G. E. J. Organomet. Chem. 1979, 181, 203-212.
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57. 1H nuclear shieldings were typically 8 ppb (β-upfield shift) and 10 ppb (α-upfield shift) per deuterium. See: Hansen, P. E. In Annual Reports on NMR Spectroscopy; Webb, G. A., Ed.; Academic Press: London, 1983; Vol. 15, pp 105-234.