Synthesis and characterization of ruthenium(II) complexes containing chiral bis(ferrocenyl) - P3 or - P2S ligands. Asymmetric transfer hydrogenation of acetophenone

Organometallics

Volumn 16, Issue 13, 1997, Pages 3004-3014

  Barbaro, Pierluigi ^a   Bianchini, Claudio ^a   Togni, Antonio ^b  

^a CNR   (Italy)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000840112     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970116c     Document Type: Article

References (84)

1. See, e.g.: Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, Germany, 1993; Vols. 1 and 2.
2. 2 symmetry, see: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
3. For a review, see: (a) Hayashi, T. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 105-142, and references cited therein. First report: (b) Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1974, 4405.
4. For a review, see: (a) Hayashi, T. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 105-142, and references cited therein. First report: (b) Hayashi, T.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1974, 4405.
5. For a brief discussion, see: (a) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475. (b) Chem. Eng. News 1996, 74(July 22), 38-40. See also: (c) McGarrity, J.; Spindler, F.; Fuchs, R.; Eyer, M. Eur. Pat. Appl. EP 624 587 A2 (LONZA AG); Chem. Abstr. 1995, 122, P81369q. (d) Spindler, F.; Pugin, B.; Jalett, H. P.; Buser, H. P.; Pittelkow, U.; Blaser, H. U. In Catalysis of Organic Reactions; Malz, R. E., Jr., Ed.; Chem. Ind. Vol. 68; Dekker: New York, 1996; pp 153-166.
6. For a brief discussion, see: (a) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475. (b) Chem. Eng. News 1996, 74(July 22), 38-40. See also: (c) McGarrity, J.; Spindler, F.; Fuchs, R.; Eyer, M. Eur. Pat. Appl. EP 624 587 A2 (LONZA AG); Chem. Abstr. 1995, 122, P81369q. (d) Spindler, F.; Pugin, B.; Jalett, H. P.; Buser, H. P.; Pittelkow, U.; Blaser, H. U. In Catalysis of Organic Reactions; Malz, R. E., Jr., Ed.; Chem. Ind. Vol. 68; Dekker: New York, 1996; pp 153-166.
7. For a brief discussion, see: (a) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475. (b) Chem. Eng. News 1996, 74(July 22), 38-40. See also: (c) McGarrity, J.; Spindler, F.; Fuchs, R.; Eyer, M. Eur. Pat. Appl. EP 624 587 A2 (LONZA AG); Chem. Abstr. 1995, 122, P81369q. (d) Spindler, F.; Pugin, B.; Jalett, H. P.; Buser, H. P.; Pittelkow, U.; Blaser, H. U. In Catalysis of Organic Reactions; Malz, R. E., Jr., Ed.; Chem. Ind. Vol. 68; Dekker: New York, 1996; pp 153-166.
8. For a brief discussion, see: (a) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475. (b) Chem. Eng. News 1996, 74(July 22), 38-40. See also: (c) McGarrity, J.; Spindler, F.; Fuchs, R.; Eyer, M. Eur. Pat. Appl. EP 624 587 A2 (LONZA AG); Chem. Abstr. 1995, 122, P81369q. (d) Spindler, F.; Pugin, B.; Jalett, H. P.; Buser, H. P.; Pittelkow, U.; Blaser, H. U. In Catalysis of Organic Reactions; Malz, R. E., Jr., Ed.; Chem. Ind. Vol. 68; Dekker: New York, 1996; pp 153-166.
9. For a brief discussion, see: (a) Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem., Int. Ed. Engl. 1996, 35, 1475. (b) Chem. Eng. News 1996, 74(July 22), 38-40. See also: (c) McGarrity, J.; Spindler, F.; Fuchs, R.; Eyer, M. Eur. Pat. Appl. EP 624 587 A2 (LONZA AG); Chem. Abstr. 1995, 122, P81369q. (d) Spindler, F.; Pugin, B.; Jalett, H. P.; Buser, H. P.; Pittelkow, U.; Blaser, H. U. In Catalysis of Organic Reactions; Malz, R. E., Jr., Ed.; Chem. Ind. Vol. 68; Dekker: New York, 1996; pp 153-166.
10. For comments concerning this point, see: Togni, A. Chimia 1996, 50, 86.
11. Barbaro, P.; Togni, A. Organometallics 1995, 14, 3570.
12. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
13. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
14. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
15. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
16. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
17. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
18. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
19. For a general review on polydentate phosphines, see: Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179. For examples of chiral tridentate phosphines, see: (a) Burk, M. J.; Harlow, R. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1462. (b) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Tetrahedron: Asymmetry 1991, 2, 569. (c) Ward, T. R.; Venanzi, L. M.; Albinati, A.; Lianza, F.; Gerfin, T.; Gramlich, V.; Ramos Tombo, G. M. Helv. Chim. Acta 1991, 74, 983. (d) Jia, G.; Lee, H. M.; Williams, I. D. Organometallics 1996, 15, 4235. (e) Heidel, H.; Scherer, J.; Asam, A.; Huttner, G.; Walter, O.; Zsolnai, L. Chem. Ber. 1995, 128, 293. (f) King, R. B.; Bakos, J.; Hoff, C. D.; Markó, L. J. Org. Chem. 1979, 44, 3095. (g) Johnson, C. R.; Imamoto, T. J. Org. Chem. 1987, 52, 2170.
20. (a) Dang, T. P.; Poulin, J. C.; Kagan, H. B. J. Organomet. Chem. 1975, 97, 105.
21. (b) Yudina, K. S.; Medved, T. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 11, 1954; Chem. Abstr. 1967, 66, 76096u.
22. (b) Yudina, K. S.; Medved, T. Y.; Kabachnik, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 11, 1954; Chem. Abstr. 1967, 66, 76096u.
23. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138.
24. Burckhardt, U.; Hintermann, L.; Schnyder, A.; Togni, A. Organometallics 1995, 14, 5415.
25. Togni, A.; Rihs, G.; Blumer, R. E. Organometallics 1992, 11, 613.
26. Stephenson, T. A.; Wilkinson, G. J. Inorg. Nucl. Chem. 1966, 28, 945.
27. Albers, M. O.; Singleton, E.; Yates, J. E. Inorg. Synth. 1989, 26, 254.
28. James, B. R.; Ochiai, E.; Rempel, G. I. Inorg. Nucl. Chem. Lett. 1971, 7, 781.
29. Schrock, R. R.; Johnson, B. F. G.; Lewis, J. J. Chem. Soc., Dalton Trans. 1974, 951.
30. Summers, M. F.; Marzilli, L. G.; Bax, A. J. Am. Chem. Soc. 1986, 108, 4285.
31. Jeener, J.; Meier, G. H.; Bachmann, P.; Ernst, R. J. Chem. Phys. 1979, 71, 4545.
32. Hayashi, T.; Yamazaki, A. J. Organomet. Chem. 1991, 413, 295.
33. Johnson, C. K. ORTEP; Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
34. Togni, A.; Breutel, C.; Soares, M. C.; Zanetti, N.; Gerfin, T.; Gramlich, V.; Spindler, F.; Rihs, G. Inorg. Chim. Acta 1994, 222, 213.
35. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
36. Crumbliss, A. L., Topping, R. J. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds.; Methods in Stereochemical Analysis 8; VCH: Weinheim, Germany, 1987; Chapter 15, p 531.
37. 13C NMR of Transition Metal Phosphine Complexes; Diehl, P., Fluck, E., Kosfeld, R., Eds.; Springer-Verlag: Berlin, 1979.
38. Jia, G.; Lee, I.; Meek, D. W.; Gallucci, J. C. Inorg. Chim. Acta 1990, 177, 81.
39. Sime, W. J.; Stephenson, T. A. J. Organomet. Chem. 1978, 161, 245.
40. Meek, D. W.; Mazanec, T. J. Acc. Chem. Res. 1981, 14, 266.
41. Armit, P. W.; Boyd, A. S. F.; Stephenson, T. A. J. Chem. Soc., Dalton Trans. 1975, 1663.
42. Hoffman, P. R.; Gaulton, K. G. J. Am. Chem. Soc. 1975, 97, 4221.
43. Jung, C. W.; Garrou, P. E.; Hoffman, P. R.; Caulton, K. G. Inorg. Chem. 1984, 23, 726.
44. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
45. Sülü, M. Dissertation, No. 10648, ETH, Zürich, 1994.
46. Albinati, A.; Jiang, Q.; Rügger, H.; Venanzi, L. M. Inorg. Chem. 1993, 32, 4940.
47. Rhodes, L. F.; Sorato, C.; Venanzi, L. M.; Bachechi, F. Inorg. Chem. 1988, 27, 604.
48. Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219.
49. Letts, J. B.; Mazanec, T. J.; Meek, D. W. Organometallics 1983, 2, 695.
50. PP = 30.1 Hz.
51. Cotton, F. A.; Hong, B. Prog. Inorg. Chem. 1992, 40, 179.
52. Schröder, M.; Stephenson, T. A. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. 4, Chapter 45.
53. (a) Bianchini, C.; Laschi, F.; Peruzzini, M.; Zanello, P. Gazz. Chim. Ital. 1994, 124, 271.
54. (b) Bianchini, C.; Masi, D.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Acta Crystallogr. 1995, C51, 2514.
55. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272.
56. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1.
57. Barbaro, P.; Bianchini, C.; Togni, A. Unpublished results.
58. (a) Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds; Wiley: New York, 1986.
59. (b) Sekine, M.; Harman, W. D.; Taube, H. Inorg. Chem. 1988, 27, 3604.
60. Sorato, C. Dissertation, No. 8775, ETH, Zürich, 1989.
61. Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585.
62. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, Germany, 1989.
63. (a) Andersson, P. G.; Harden, A.; Tanner, D.; Norrby, P. O. Helv. Chim. Acta 1995, 1, 12.
64. (b) von Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Rüegger, H.; Pregosin, P. S. Helv. Chim. Acta 1995, 78, 265.
65. (c) Barbara, P.; Pregosin, P. S.; Salzmann, R.; Albinati, A.; Kunz, R. W. Organometallics 1995, 14, 5160.
66. Motschi, H.; Pregosin, P. S.; Venanzi, L. M. Helv. Chim. Acta 1979, 62, 667.
67. For a review on asymmetric hydrogen transfer reactions to ketones, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
68. For literature data before 1993 on asymmetric hydrogen transfer from i-PrOH to acetophenone, see ref 1, Vol. 1.
69. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
70. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
71. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
72. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
73. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
74. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
75. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
76. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
77. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
78. For recent examples on asymmetric hydrogen transfer from i-PrOH to acetophenone see: (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562. (b) Takehara, J.; Hashiguchi, S.; Fujii, A.; Inoue, S.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1996, 233. (c) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (d) Gamez, P.; Fache, Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (e) Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. (f) Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800. (g) Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087. (h) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215. For recent examples of base-assisted hydrogenations of acetophenone see: (i) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (j) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Org. Synth. 1993, 71, 1.
79. (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, Germany, 1993.
80. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
81. For examples on asymmetric hydrogen transfer to ketones using formic acid, see: (a) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (b) Wagner, K. Angew. Chem., Int. Ed. Engl. 1970, 9, 50.
82. For examples on asymmetric hydrogen transfer to ketones using formic acid, see: (a) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521. (b) Wagner, K. Angew. Chem., Int. Ed. Engl. 1970, 9, 50.
83. (a) Bianchini, C.; Farnetti, E.; Graziani, M.; Peruzzini, M.; Polo, A. Organometallics 1993, 12, 3753.
84. (b) Bianchini, C.; Farnetti, E.; Glendenning, L.; Graziani, M.; Nardini, G.; Peruzzini, M.; Rocchini, E.; Zanobini, F. Organometallics 1995, 14, 1489.