Cis-β-bis(carbonyl) ruthenium-salen complexes: X-ray crystal structures and remarkable catalytic properties toward asymmetric intramolecular alkene cyclopropanation

Journal of the American Chemical Society

Volumn 131, Issue 12, 2009, Pages 4405-4417

  Xu, Zhen Jiang ^a   Fang, Ran ^b   Zhao, Cunyuan ^b   Huang, Jie Sheng ^c   Li, Gong Yong ^a   Zhu, Nianyong ^c   Che, Chi Ming ^a,c  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SUN YAT SEN UNIVERSITY   (China)

^c UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; CARBENE; CARBENOID; CATALYTIC PROPERTIES; COORDINATION MODES; CYCLOPROPANATION; CYCLOPROPYL; DFT CALCULATION; DIANION; INTRAMOLECULAR CYCLOPROPANATION; LIGHT IRRADIATIONS; MODEL CATALYSTS; SALEN COMPLEX; TRANSFER REACTION; TRANSITION STATE; TRICHLOROBENZENE; X RAY CRYSTAL STRUCTURES;

COORDINATION REACTIONS; ENANTIOSELECTIVITY; OLEFINS; ORGANIC COMPOUNDS; RUTHENIUM; SULFUR COMPOUNDS; X RAY CRYSTALLOGRAPHY;

RUTHENIUM COMPOUNDS;

ALKENE; BETA BIS(CARBONYL) RUTHENIUM SALEN COMPLEX; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; CARBON; HYDROGEN; LIGAND; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; CYCLOPROPANATION; ENANTIOSELECTIVITY; IRRADIATION; X RAY CRYSTALLOGRAPHY; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; PROCEDURES; THERMODYNAMICS;

ALKENES; CARBON; CATALYSIS; CHEMISTRY, ORGANIC; CRYSTALLOGRAPHY, X-RAY; HYDROGEN; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RUTHENIUM; THERMODYNAMICS;

EID: 67849105121     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8086399     Document Type: Article

References (115)

1. For recent reviews, see: (a) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189.
2. (b) Yamada, S. Coord. Chem. Rev. 1999, 190-192, 537.
3. (c) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
4. (d) Atwood, D. A.: Harvey, M. J. Chem. Rev. 2001, 101, 37.
5. (e) Kojima, M.; Taguchi, H.; Tsuchimoto, M.; Nakajima, K. Coord. Chem. Rev. 2003, 237, 183.
6. (f) Tsuchida, E.; Oyaizu, K. Coord. Chem. Rev. 2003, 237, 213.
7. (g) Katsuki, T. Synlett 2003, 281.
8. (h) Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410.
9. (i) Katsuki, T. Chem. Soc. Rev. 2004, 33, 437.
10. (j) Darens- bourg, D. J.; Mackiewicz, R. M.; Phelps, A. L.; Billodeaux, D. R. Acc. Chem. Res. 2004, 37, 836.
11. (k) Venkataramanan, N. S.; Kuppuraj, G.; Rajagopal, S. Coord. Chem. Rev. 2005, 249, 1249.
12. (l) McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563.
13. (m) Baleizao, C.; Garcia, H. Chem. Rev. 2006, 106, 3987.
14. (n) Matsumoto, K.; Saito, B.; Katsuki, T. Chem. Commun. 2007, 3619.
15. (a) Herrmann, W. A.; Rauch, M. U.; Artus, G. R. J. Inorg. Chem. 1996, 35, 1988.
16. (b) Munslow, I. J.; Gillespie, K. M.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 1638.
17. (c) Knight, P. D.; Scott, P. Coord. Chem. Rev. 2003, 242, 125.
18. (d) Che, C.-M.; Huang, J.-S. Coord. Chem. Rev. 2003, 242, 97.
19. Sauve, A. A.; Groves, J. T. J. Am. Chem. Soc. 2002, 124, 4770.
20. (a) Thornback, J. R.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1978, 110.
21. (b) Leung, W. H.; Chan, E. Y. Y.; Chow, E. K. F.; Williams, I. D.; Peng, S. M. J. Chem. Soc., Dalton Trans. 1996, 1229.
22. (a) Khavrutskii, I. V.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 2003, 125, 13879.
23. (b) Khavrutskii, I. V.; Musaev, D. G.; Morokuma, K. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5743.
24. Li, G.-Y.; Zhang, J.; Chan, P. W. H.; Xu, Z.-J.; Zhu, N.; Che, C.-M. Organometallics 2006, 25, 1676.
25. (a) Odenkirk, W.; Rheingold, A. L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392.
26. (b) Nakajima, K.; Ando, Y.; Mano, H.; Kojima, M. Inorg. Chim. Acta 1998, 274, 184.
27. (c) Takeda, T.; Irie, R.; Katsuki, T. Synlett 1999, 1166.
28. (d) Works, C. F.; Jocher, C. J.; Bart, G. D.; Bu, X.; Ford, P. C. Inorg. Chem. 2002, 41, 3728.
29. (e) Bordini, J.; Hughes, D. L.; Da Motta Neto, J. D.; da Cunha, C. J. Inorg. Chem. 2002, 41, 5410.
30. (f) Miller, J. A.; Hennessy, E. J.; Marshall, W. J.; Scialdone, M. A.; Nguyen, S. T. J. Org. Chem. 2003, 68, 7884.
31. (g) Man, W.-L.; Tang, T.-M.; Wong, T.-W.; Lau, T.-C.; Peng, S.-M.; Wong, W.-T. J. Am. Chem. Soc. 2004, 126, 478.
32. (h) Man, W.-L.; Lam, W. W. Y.; Yiu, S.-M.; Lau, T.-C.; Peng, S.-M. J. Am. Chem. Soc. 2004, 126, 15336.
33. (i) Yeung, W.-F.; Lau, P.-H.; Lau, T.-C.; Wei, H.-Y.; Sun, H.-L.; Gao, S.; Chen, Z.-D.; Wong, W.-T. Inorg. Chem. 2005, 44, 6579.
34. (j) Wong, C.-Y.; Man, W.-L.; Wang, C.; Kwong, H.- L.; Wong, W.-Y.; Lau, T.-C. Organometallics 2008, 27, 324.
35. (k) Man, W.-L.; Kwong, H.-K.; Lam, W. W. Y.; Xiang, J.; Wong, T.-W.; Lam, W.-H.; Wong, W.-T.; Peng, S.-M.; Lau, T.-C. Inorg. Chem. 2008, 47, 5936.
36. 4b
37. (a) Doyle, M. P.; Pieters, R. J.; Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Müller, P. J. Am. Chem. Soc. 1991, 113, 1423.
38. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763.
39. A1)(CO)].
40. Selected reviews: (a) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 387.
41. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
42. (c) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
43. A catalysts, see: (a) Bosnich, B. Aldrichimica Acta 1998, 31, 76.
44. (b) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
45. (c) Nishiyama, H. Top. Organomet. Chem. 2004, 11, 81.
46. (d) Yamamoto, Y.; Itoh, K. Top. Organomet. Chem. 2004, 11, 249.
47. (e) Arends, I. W. C. E.; Kodama, T.; Sheldon, R. A. Top. Organomet. Chem. 2004, 11, 277.
48. (f) Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
49. (g) Irie, R.; Katsuki, T. Chem. Rec. 2004, 4, 96.
50. (h) Chatterjee, D. Coord. Chem. Rev. 2008, 252, 176.
51. Leung, W.-H.; Che, C.-M. Inorg. Chem. 1989, 28, 4619.
52. (a) Odenkirk, W.; Whelan, J.; Bosnich, B. Tetrahedron Lett. 1992, 33, 5729.
53. (b) Ellis, W. W.; Odenkirk, W.; Bosnich, B. Chem. Commun. 1998, 1311.
54. (a) Takeda, T.; Irie, R.; Shinoda, Y.; Katsuki, T. Synlett 1999, 1157.
55. (b) Nakata, K.; Takeda, T.; Mihara, J.; Hamada, T.; Irie, R.; Katsuki, T. Chems Eur. J. 2001, 7, 3776.
56. Mihara, J.; Hamada, T.; Takeda, T.; Irie, R.; Katsuki, T. Synlett 1999, 1160.
57. (a) Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1163.
58. (b) Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1793.
59. (c) Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron 2000, 56, 3501.
60. (d) Uchida, T.; Katsuki, T. Synthesis 2006, 1715.
61. (a) Saha, B.; Uchida, T.; Katsuki, T. Synlett 2001, 114.
62. (b) Uchida, T.; Saha, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 2521.
63. (c) Saha, B.; Uchida, T.; Katsuki, T. Tetrahedron: Asymmetry 2003, 14, 823.
64. (a) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119.
65. (b) Miyata, A.; Murakami, M.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2001, 42, 7067.
66. (a) Murakami, M.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 7071.
67. (b) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301.
68. Omura, K.; Murakami, M.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 354.
69. (a) Shimizu, H.; Katsuki, T. Chem. Lett. 2003, 32, 480.
70. (b) Shimizu, H.; Onitsuka, S.; Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2005, 127, 5396.
71. (c) Nakamura, Y.; Egami, H.; Matsumoto, K.; Uchida, T.; Katsuki, T. Tetrahedron 2007, 63, 6383.
72. (a) Miller, J. A.; Jin, W.; Nguyen, S. T. Angew. Chem., Int. Ed. 2002, 41, 2953.
73. (b) Miller, J. A.; Gross, B. A.; Zhuravel, M. A.; Jin, W.; Nguyen, S. T. Angew. Chem., Int. Ed. 2005, 44, 3885.
74. Liang, J.-L.; Yu, X.-Q.; Che, C.-M. Chem. Commun. 2002, 124.
75. Bhowon, M. G.; Wah, H. L. K.; Narain, R. Polyhedron 1999, 18, 341.
76. (a) Flower, K. R.; Lightfoot, A. P.; Wan, H.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2002, 2058.
77. (b) Howard, J. A. K.; Ilyashenko, G.; Sparkes, H. A.; Whiting, A. Dalton Trans. 2007, 2108.
78. Kumar, K. N.; Ramesh, R. Polyhedron 2005, 24, 1885.
79. Fujita, H.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Lett. 2007, 36, 1092.
80. Yeori, A.; Gendler, S.; Groysman, S.; Goldberg, I.; Kol, M. Inorg. Chem. Commun. 2004, 7, 280.
81. (a) Saito, B.; Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2007, 129, 1978.
82. (b) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
83. (c) Chen, P.; Chisholm, M. H.; Gallucci, J. C.; Zhang, X.; Zhou, Z. Inorg. Chem. 2005, 44, 2588.
84. For reviews including transition-metal-catalyzed asymmetric intramolecular cyclopropanation, see: (a) Ref 11.
85. (b) Doyle, M. P.; Hu, W. Synlett 2001, 1364.
86. (c) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
87. (d) Doyle, M. P. Top. Organomet. Chem. 2004, 13, 203.
88. (e) Doyle, M. P. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 341.
89. Doyle, M. P.; Zhou, Q.-L.; Dyatkin, A. B.; Ruppar, D. A. Tetrahedron Lett. 1995, 36, 7579.
90. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry 1995, 6, 2487.
91. Che, C.-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.- L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.-M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119.
92. 1 would be an unfavorable pathway due to the steric hindrance of the phenyl group. See: Fang, R.; Ke, Z.; Shen, Y.; Zhao, C.; Phillips, D. L. J. Org. Chem. 2007, 72, 5139.
93. (a) Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770.
94. (b) Houk, K. N.; Rondan, N. G.; Mareda, J. J. Am. Chem. Soc. 1984, 106, 4291.
95. (c) Blake, J. F.; Wierschke, S. G.; Jorgenson, W. L. J. Am. Chem. Soc. 1989, 111, 1919.
96. (d) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 10805.
97. (e) Bernardi, F.; Bottoni, A.; Canepa, C.; Olivucci, M.; Robb, M. A.; Tonachini, G. J. Org. Chem. 1997, 62, 2018.
98. Deng, Li; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320.
99. Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851.
100. Takenaka, N.; Huang, Y.; Rawal, V. H. Tetrahedron 2002, 58, 8299.
101. Otwinowski, Z.; Minor, W. In Methods in Enzymology: Macromolecular Crystallography; Part A., Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, p 307.
102. Sheldrick, G. M. SHELXS-97. Program for the Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
103. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
104. Sheldrick, G. M. SHELXL-97. Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
105. Frisch, M. J.; Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford CT, 2004.
106. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785.
107. (a) Jursic, B.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1995, 1223.
108. (b) Jursic, B. S. Chem. Phys. Lett. 1996, 256, 603.
109. (c) Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 425, 193.
110. (d) Jursic, B. S. J. Mol. Struct. (THEOCHEM) 1998, 452, 145.
111. (a) Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. J. Comput. Chem. 2001, 22, 976.
112. (b) Rassolov, V. A.; Pople, J. A.; Ratner, M. A.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223.
113. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
114. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
115. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.