Five-coordinate [RuCl(P-P *)2]+ complexes containing chiral diphosphines: Application in the asymmetric cyclopropanation and epoxidation of olefins

Organometallics

Volumn 18, Issue 26, 1999, Pages 5691-5700

  Stoop, Robert M ^a   Bauer, Christian ^a   Setz, Patrick ^a   Wörle, Michael ^a   Wong, Terrance Y H ^a   Mezzetti, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000148948     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990657x     Document Type: Article

References (88)

1. For a review, see: Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. Homogeneous Hydrogenation; Kluwer: Dordrecht, 1994; Chapter 1.
2. See, for instance: (a) Cornils, B.; Herrmann, W. A. Applied Homogeous Catalysis with Organometallic Compounds, 1st ed.; VCH: New York, 1996; Vols. 1-2.
3. (b) Doyle, M. P.; McKervey, A. M.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazocompounds, from Cyclopropanes to Ylides, 1st ed.; Wiley: New York, 1998.
4. See, for instance: (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993; Chaper 4.2.
5. (b) Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603.
6. (c) Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
7. (d) Lin, Z.; Hall, M. B. Coord. Chem. Rev. 1993, 123, 149.
8. (e) Drago, R. S. Coord. Chem. Rev. 1992, 117, 185.
9. (f) Jørgensen, K. A. Chem. Rev. 1989, 89, 431.
10. Recent papers: (a) Gross, Z.; Ini, S. Inorg. Chem. 1999, 38, 1446.
11. (b) Lai, T. S.; Kwong, H. L.; Zhang, R.; Che, C. M. J. Chem. Soc., Dolton Trans. 1998, 3559.
12. (c) Berkessel A.; Frauenkron, M. J. Chem. Soc., Perkin Trans. 1997, 2265.
13. (d) Galardon, E.; Roue, S.; Le Maux, P.; Simonneaux, G. Tetrahedron Lett. 1998, 36, 2333.
14. (e) Berkessel, A.; Frauenkron, M. Tetrahedron Lett. 1997, 38, 7175.
15. (f) Lo, W. C.; Cheng, K. F.; Che, C. M.; Mak, T. C. W. Chem. Commun. 1997, 1205.
16. Recent papers: (a) Cheng, M. C.; Chan, M. C. W.; Peng, S. M.; Cheung, K. K.; Che, C. M. J. Chem. Soc., Dalton Trans. 1997, 3479.
17. (b) Kureshi, R. I.; Khan, N. H.; Abdi, S. H. R.; Iyer, P. J. Mol. Catal. A-Chem. 1997, 124, 91.
18. (c) Bernardo, K.; Leppard, S.; Robert, A.; Commenges, G.; Dahan, F.; Meunier, B. Inorg. Chem. 1996, 35, 387.
19. See, for instance: (a) End, N.; Pfaltz, A. Chem. Commun. 1998, 589.
20. (b) Mizushima, K.; Nakaura, M.; Park, S. B.; Nishiyama, H.; Monjushiro, H.; Harada, K.; Haga, M. Inorg. Chim. Acta 1997, 261, 175.
21. Recent papers: (a) Stoop, R. M.; Mezzetti, A. Green Chem. 1999, 39.
22. (b) Song, J.-H.; Cho, D.-J.; Jeon, S.-J.; Kim, Y.-H.; Kim, T.-J.; Jeong, J H. Inorg. Chem. 1999, 38, 893.
23. Recent papers: (a) Lee, H. M.; Bianchini, C.; Jia, G. C.; Barbaro, P. Organometallics 1999, 18, 1961. (b) Barbaro, P.; Bianchini, C.; Togni, A. Organometallics 1997, 16, 3004. (c) Nishiyama, H.; Soeda, N.; Naito, T.; Motoyama, Y. Tetrahedron: Asymmetry 1998, 9, 2865.
24. Recent papers: (a) Lee, H. M.; Bianchini, C.; Jia, G. C.; Barbaro, P. Organometallics 1999, 18, 1961. (b) Barbaro, P.; Bianchini, C.; Togni, A. Organometallics 1997, 16, 3004. (c) Nishiyama, H.; Soeda, N.; Naito, T.; Motoyama, Y. Tetrahedron: Asymmetry 1998, 9, 2865.
25. Recent papers: (a) Lee, H. M.; Bianchini, C.; Jia, G. C.; Barbaro, P. Organometallics 1999, 18, 1961. (b) Barbaro, P.; Bianchini, C.; Togni, A. Organometallics 1997, 16, 3004. (c) Nishiyama, H.; Soeda, N.; Naito, T.; Motoyama, Y. Tetrahedron: Asymmetry 1998, 9, 2865.
26. See, for instance: (a) Nishiyama, H.; Shimada, T.; Ito, H.; Sugiyama, H.; Motoyama, Y. Chem. Commun. 1997, 1863. (b) Cetinkaya, B.; Cetinkaya, E.; Brookhart, M.; White, P. S. J. Mol. Catal. A-Chem. 1999, 142, 101.
27. See, for instance: (a) Nishiyama, H.; Shimada, T.; Ito, H.; Sugiyama, H.; Motoyama, Y. Chem. Commun. 1997, 1863. (b) Cetinkaya, B.; Cetinkaya, E.; Brookhart, M.; White, P. S. J. Mol. Catal. A-Chem. 1999, 142, 101.
28. Recent papers: (a) Barf, G. A.; van den Hoek, D.; Sheldon, R. A. Tetrahedron 1996, 52, 12971. (b) Boelrijk, A. E. M.; Neenan, T. X.; Reedijk, J. J. Chem. Soc., Dalton Trans. 1997, 4561. (c) Augier, C.; Malara, L.; Lazzeri, V.; Waegell, B. Tetrahedron Lett. 1995, 36, 8775.
29. Recent papers: (a) Barf, G. A.; van den Hoek, D.; Sheldon, R. A. Tetrahedron 1996, 52, 12971. (b) Boelrijk, A. E. M.; Neenan, T. X.; Reedijk, J. J. Chem. Soc., Dalton Trans. 1997, 4561. (c) Augier, C.; Malara, L.; Lazzeri, V.; Waegell, B. Tetrahedron Lett. 1995, 36, 8775.
30. Recent papers: (a) Barf, G. A.; van den Hoek, D.; Sheldon, R. A. Tetrahedron 1996, 52, 12971. (b) Boelrijk, A. E. M.; Neenan, T. X.; Reedijk, J. J. Chem. Soc., Dalton Trans. 1997, 4561. (c) Augier, C.; Malara, L.; Lazzeri, V.; Waegell, B. Tetrahedron Lett. 1995, 36, 8775.
31. (a) Bressan, M.; Morvillo, A. Inorg. Chem. 1989, 28, 950.
32. (b) Morvillo, A.; Bressan, M. J. Mol. Catal. A-Chem. 1997, 125, 119.
33. (c) Maran, F.; Morvillo, A.; d'Alessandro, N.; Bressan, M. Inorg. Chim. Acta 1999, 288, 122.
34. Bressan, M.; Rigo, P. Inorg. Chem. 1975, 14, 2286.
35. (a) Noyori, R.; Takaya, H. Ace. Chem. Res. 1990, 23, 345.
36. (b) Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H.-J. Helv. Chim. Acta 1988, 71, 897.
37. (c) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
38. (d) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668.
39. (e) Mezzetti, A.; Tschumper, A.; Consiglio, G. J. Chem. Soc., Dalton Trans. 1995, 49.
40. See for instance: Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
41. Jugé, S.; Stéphan, M.; Laffitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357.
42. Yoshikuni, T.; Bailar, J. C. Inorg. Chem. 1982, 21, 2129.
43. 2] has been briefly reported previously: (a) Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922. (b) James, B. R.; Fogg, D. E. J. Organomet. Chem. 1993, 462, C21.
44. 2] has been briefly reported previously: (a) Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922. (b) James, B. R.; Fogg, D. E. J. Organomet. Chem. 1993, 462, C21.
45. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1.
46. Polam, J. R.; Porter, L. C. J. Coord. Chem. 1993, 29, 109.
47. Wartchow, R.; Berthold, H. J Z. Kristallogr. 1977, 145, 240.
48. Jeffery, J. C.; Jelliss, P. A.; Lebedev, V. N.; Stone, F. G. A. Organometallics 1996, 15, 4737.
49. (a) Caulton, K. G. New J. Chem. 1994, 18, 25.
50. (b) Riehl, J.-F.; Jean, Y.; Eisenstein, O.; Pélissier, M. Organometallics 1992, 11, 729.
51. (c) Johnson, T. J.; Folting, K.; Streib, W. E.; Martin, J. D.; Huffman, J. C.; Jackson, S. A.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1995, 34, 488, and references therein.
52. In the first molecule, Ru, P(3), P(4), and C(3) are perfectly coplanar, with C(4) at 0.74 Å from their plane, whereas Ru, P(1), P(2), and C(2) are coplanar within ±0.09 A, and C(1) is displaced by 0.70 Å from the mean plane.
53. Mezzetti, A.; Del Zotto, A.; Rigo, P.; Bresciani Pahor, N. J. Chem. Soc., Dalton Trans. 1989, 1045.
54. Batista, A. A.; Centeno Cordeiro, L. A.; Oliva, G. Inorg. Chim. Acta 1993, 203, 185.
55. Chin, B.; Lough, A. J.; Morris, R. H.; Schweitzer C. T.; D'Agostino, C. Inorg. Chem. 1994, 33, 6278.
56. The next closest contact is Ru⋯C(22) (3.61(1) Å).
57. (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1.
58. (b) Crabtree, R. H.; Holt, E. M.; Lavin, M.; Morehouse, S. M. Inorg. Chem. 1985, 24, 1986.
59. (c) Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1993, 32, 789.
60. (d) Yao, W.; Eisenstein, O.; Crabtree, R. Inorg. Chim. Acta 1997, 254, 105.
61. (a) Cooper, A. C.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 9069.
62. (b) Ujaque, G.; Cooper, A. C.; Maseras, F.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1998, 120, 361.
63. For recent examples, see: (a) Martelletti, A.; Gramlich, V.; Zürcher, F.; Mezzetti, A. New J. Chem. 1999, 199. (b) Baratta, W.; Herdtweck, E.; Rigo, P.Angew. Chem. 1999, 111, 1733. (c) Huang, D.; Huffman, J. C.; Bollinger, J C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (d) Huang, D.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2004. (e) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
64. For recent examples, see: (a) Martelletti, A.; Gramlich, V.; Zürcher, F.; Mezzetti, A. New J. Chem. 1999, 199. (b) Baratta, W.; Herdtweck, E.; Rigo, P.Angew. Chem. 1999, 111, 1733. (c) Huang, D.; Huffman, J. C.; Bollinger, J C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (d) Huang, D.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2004. (e) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
65. For recent examples, see: (a) Martelletti, A.; Gramlich, V.; Zürcher, F.; Mezzetti, A. New J. Chem. 1999, 199. (b) Baratta, W.; Herdtweck, E.; Rigo, P.Angew. Chem. 1999, 111, 1733. (c) Huang, D.; Huffman, J. C.; Bollinger, J C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (d) Huang, D.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2004. (e) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
66. For recent examples, see: (a) Martelletti, A.; Gramlich, V.; Zürcher, F.; Mezzetti, A. New J. Chem. 1999, 199. (b) Baratta, W.; Herdtweck, E.; Rigo, P.Angew. Chem. 1999, 111, 1733. (c) Huang, D.; Huffman, J. C.; Bollinger, J C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (d) Huang, D.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2004. (e) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
67. For recent examples, see: (a) Martelletti, A.; Gramlich, V.; Zürcher, F.; Mezzetti, A. New J. Chem. 1999, 199. (b) Baratta, W.; Herdtweck, E.; Rigo, P.Angew. Chem. 1999, 111, 1733. (c) Huang, D.; Huffman, J. C.; Bollinger, J C.; Eisenstein, O.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 7398. (d) Huang, D.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2004. (e) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
68. Seebach, D.; Devaquet, E.; Ernst, A.; Hayakawa, M.; Kühnle, F. N. M.; Schweizer, W. B.; Weber, B. Helv. Chim. Acta 1995, 78, 1636.
69. (a) Orpen, A. G. Chem. Soc. Rev. 1993, 22, 191.
70. (b) Halpern, J. Science 1982, 217, 401.
71. 2)((R,S)-chiraphos)]: Gugger, P.; Limmer, S. O.; Watson, A. A.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1993, 32, 5692.
72. Brown, J. M.; Evans, P. L.; Maddox, P. J.; Sutton, K. H. J. Organomet. Chem. 1989, 359, 115.
73. Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Kondo, M.; Kitagawa, S. J. Organomet. Chem. 1997, 538, 199.
74. Schenk, W. A.; Frisch, J.; Dürr, M.; Burzlaff, N.; Stalke, D.; Fleischer, R.; Adam, W.; Prechtl, F.; Smerz, A. K. Inorg. Chem. 1997, 36, 2372.
75. (a) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., Ill; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
76. (b) Rappé, A. K.; Colwell, K. S.; Casewit, C. J. Inorg. Chem. 1993, 32, 3438.
77. Mezzetti, A.; Rigo, P. Unpublished results.
78. For selected papers on ruthenium catalysts with monodentate phosphines, see: Demonceau, A.; Simal, F.; Jan, D.; Noels, A. F. Tetrahedron Lett. 1999, 40, 1653, and references therein.
79. 39b (b) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
80. However, the use of 5 mol % of the catalyst did not improve either conversion or ee.
81. See, for instance: (a) Galardon, E.; Le Maux, P.; Toupet, L.; Simmoneaux, G. Organometallics 1998, 17. 565.
82. (b) Nishiyama, H.; Aoki, K.; Itoh, H.; Iwamura, T.; Sakata, N.; Kurihara, O.; Motoyama, Y. Chem. Lett. 1996, 1071.
83. Barf, G. A.; Sheldon, R. A. J. mol. Catal. A-Chem. 1995, 102, 23.
84. Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
85. Sinigalia, R.; Michelin, R. A.; Pinna, F.; Strukul, G. Organometallics 1987, 6, 728.
86. Barthazy, P.; Wörle, M.; Mezzetti, A. J. Am. Chem. Soc. 1999, 121, 480.
87. However, metal-PhIO adducts have been suggested to react with olefins without the intermediacy of a metal-oxo species: Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7195.
88. Hallman, P. S.; Stephenson, T. A.; Wilkinson, G. Inorg. Synth. 1970, 12, 237.