2-Azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3116-3122

  Alonso, Diego A ^a   Nordin, Sofia J M ^a   Roth, Peter ^a   Tarnai, Tibor ^a   Andersson, Pher G ^a   Thommen, Marc ^b   Pittelkow, Ulrich ^b  

^a UPPSALA UNIVERSITY   (Sweden)

^b SOLVIAS AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; REDUCTION; SYNTHESIS;

EID: 0034685971     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991914a     Document Type: Article

References (64)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley: New York, 1994.
2. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Berlin, 1993.
3. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1986.
4. (a) Corey, E: J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
5. (b) Corey, E: J.; Bakshi, R. K.; Shibata, S.; Chen, C.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
6. Wallbaum, S.; Martens, J. Tetrahedron Asymmetry 1992, 3, 1475.
7. Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hiraou, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2039.
8. Noyori, R.; Takaya, H. Acta Chem. Scand. 1996, 50, 380.
9. (a) Nishibayashi, Y.; Takei, S.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2291.
10. (b) Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817.
11. Bernard, M.; Guiral, V.; Delbecq, F.; Fache, F.; Sautet, P.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441. For reviews, see:
12. Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
13. (e) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045.
14. (a) Sasson, Y.; Blum, J. Tetrahedron Lett. 1971, 24, 2167.
15. (b) Sasson, Y.; Blum, J. J. Org. Chem. 1975, 40, 1887.
16. Linn, D. E.; Halpern, G. J. Am. Chem. Soc. 1987, 109, 2969.
17. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
18. (e) Chowdhury, R. L.; Bäckvall, J. E. J. Chem. Soc., Chem. Commun. 1991, 1063.
19. Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800.
20. (a) Gladiali, S.; Pinna, L.; Delogu, G.; De Martin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635.
21. (b) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705.
22. Gamez, P.; Dunjic, B.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441.
23. Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 65, 2186.
24. (a) Zassinovich, G.; Bettella, R.; Mestroni, G.; Breciani-Pahor, N.; Geremia, S., Randaccio, L. J. Organomet. Chem. 1989, 370, 187.
25. (b) Mashima, K.; Akutawa, T.; Zhang, X.; Takaya, H.; Taketomi, T.; Kumobayashi, H.; Akutagawa, S. J. Organomet. Chem. 1992, 428, 213.
26. Bianchini, C.; Farnetti, E.; Glendenning, L.; Graziani, M.; Nardin, G.; Peruzzini, M.; Rocchini, E.; Zanobini, F. Organometallics 1995, 14, 1489.
27. Inoue, S.; Nomura, K.; Hashiguchi, Sh.; Noyori, R.; Izawa, Y. Chem. Lett. 1997, 957.
28. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
29. (b) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
30. Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
31. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
32. (e) Murata, K.; Okano, K.; Miyagi, M.; Iwane, H.; Noyori, R.; Ikariya, T. Org. Lett. 1999, 1, 1119.
33. (a) Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
34. (b) Genet, J.-P.; Ratovelomonana-Vidal, V.; Pinel, C. Synlett 1993, 34, 478.
35. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347.
36. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc., Chem. Commun. 1995, 1721.
37. (e) Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381.
38. (f) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599.
39. (g) Jiang, Q.; Van Plew, D.; Mutuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797.
40. (h) Gamez, P.; Dunjic, B.; Lemaire, M. J. Org. Chem. 1996, 61, 5196.
41. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
42. (j) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104.
43. (k) Schwink, L.; Ireland, T.; Püntener, K.; Knochel, P. Tetrahedron: Asymmetry 1998, 9, 1143.
44. Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817.
45. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2291.
46. (a) Takehara, J.; Hashiguchi, S.; Fujii, A.; Invoe, S.-I.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233.
47. (b) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
48. Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226.
49. Kenny, J. A.; Palmer, M. J.; Smith, A. R. C.; Walsgrove, T.; Wills, M. Synlett 1999, 10, 1615.
50. Alonso, D. A.; Guijarro, D.; Pinho, P.; Temme, O.; Andersson, P. G. J. Org. Chem. 1998, 63, 2749.
51. (a) Stella, L.; Abraham, M.; Feneau-Dupont, J.; Tinant, B.; Declercq, J. P. Tetrahedron Lett. 1990, 18, 2603.
52. (b) Waldmann, H.; Braun, M. Liebigs Ann. Chem. 1991, 1045.
53. Bailey, P. D.; Brown, G. R.; Korber, F.; Reed, A.; Willson, R. D. Tetrahedron: Asymmetry 1991, 12, 1263.
54. Alonso, D. A.; Brandt, P.; Nordin, S. J. M.; Andersson, P. G. J. Am. Chem. Soc. 1999, 121, 9580.
55. Alonso, D. A.; Nordin, S. J. M.; Andersson, P. G. Unpublished results.
56. Brandt, P.; Hedberg, Ch.; Lawonn, K.; Pinho, P.; Andersson, P. G. Chem. Eur. J. 1999, 5, 1692.
57. For the synthesis of the Ru complexes, see: (a) Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233.
58. (b) Bennett, M. A.; Matheson, T. W.; Robertson, G. B.; Smith, A. K.; Tucker, P. A. Inorg. Chem. 1980, 19, 101.
59. Alonso, D. A.; Nordin, S. J. M.; Andersson, P. G. Org. Lett. 1999, 1, 1595.
60. Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922.
61. Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1987, 62, 2518.
62. Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707.
63. Pinho, P.; Guijarro, D.; Andersson, P. G. Tetrahedron 1998, 54, 7897.
64. Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 8, 2530.