Enantioselective intramolecular cyclopropanation of cis-alkenes by chiral ruthenium (II) Schiff base catalysts and crystal structures of (Schiff base) ruthenium complexes containing carbene, PPh3, and CO ligands

Organometallics

Volumn 25, Issue 7, 2006, Pages 1676-1688

  Li, Gong Yong ^a   Zhang, Jing ^b   Chan, Philip Wai Hong ^b   Xu, Zhen Jiang ^a   Zhu, Nianyong ^b   Che, Chi Ming ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; PORPHYRINS;

CYCLOPROPANATION; DIAZOACETATES; ENANTIOSELECTIVITIES; X-RAY CRYSTAL STRUCTURE;

ORGANOMETALLICS;

EID: 33645813799     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om051009i     Document Type: Article

References (97)

1. (a) Donaldson, W. A. Tetrahedron 2001, 57, 8589.
2. (b) Doyle, M. P.; Ren, T. Prog. Inorg. Chem. 2001, 49, 113.
3. (c) Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
4. (d) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
5. (e) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
6. (f) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385.
7. (g) Salaün, J. Chem. Rev. 1989, 89, 1247.
8. (a) Katsuki, T. Compr. Coord. Chem. II 2004, 9, 207.
9. (b) Maas, G. Chem. Soc. Rev. 2004, 33, 183.
10. (c) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
11. (d) Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1.
12. (e) Che, C.-M.; Huang, J.-S. Coord. Chem. Rev. 2002, 231, 151.
13. (f) Simonneaux, G.; Le Maux, P. Coord. Chem. Rev. 2002, 228, 43.
14. (g) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998.
15. For examples using copper(I) catalysts, see: (a) Sawada, T.; Nakada, M. Adv. Synth. Catal. 2005, 347, 1527.
16. (b) Doyle, M. P.; Hu, W. Tetrahedron Lett. 2000, 41, 6265.
17. (c) Doyle, M. P.; Hu, W. H.; Chapman, B.; Marnett, A. B.; Peterson, C. S.; Vitale, J. P.; Stanley, S. A. J. Am. Chem. Soc. 2000, 122, 5718.
18. (d) Doyle, M. P.; Hu, W.; Phillips, I. M.; Wee, A. G. H. Org. Lett. 2000, 2, 1777.
19. (e) Doyle, M. P.; Chapman, B. J.; Hu, W.; Peterson, C. S.; McKervey, M. A.; Garcia, C. F. Org. Lett. 1999, 1, 1327.
20. (f) Sato, H.; Kim, Y. S.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 2973.
21. (g) Tokunoh, R.; Tomiyama, H.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 2449.
22. (h) Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
23. (i) Piqué, C.; Fähndrich, B.; Pfaltz, A. Synlett 1995, 491.
24. For examples using dirhodium(II,II) catalysts, see: (a) Lin, W.; Charette, A. B. Adv. Synth. Catal. 2005, 347, 1547.
25. (b) Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667.
26. (c) Barberis, M.; Pérez-Prieto, J.; Stiriba, S.-E.; Lahuerta, P. Org. Lett. 2001, 21, 3317.
27. (d) Barberis, M.; Lahuerta, P.; Pérez-Prieto, J.; Sanaú, M. Chem. Commun. 2001, 439.
28. (e) Doyle, M. P.; Hu, W. Adv. Synth. Catal. 2001, 343, 299.
29. (f) Davies, H. M. L.; Calvo, R. L.; Townsend, R. J.; Ren, P.; Churchill, R. M. J. Org. Chem. 2000, 65, 4261.
30. (g) Davies, H. M. L.; Doan, B. D. J. Org. Chem. 1999, 64, 8501.
31. (h) Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179.
32. (i) Doyle, M. P.; Zhou, Q.-L.; Dyatkin, A. B.; Ruppar, D. A. Tetrahedron Lett. 1995, 36, 7579.
33. (j) Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941.
34. (k) 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.
35. (1) Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493.
36. (m) Doyle, M. P.; Pieters, R. J.; Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Mueller, P. J. Am. Chem. Soc. 1991, 113, 1423.
37. Doyle, M. P.; Hu, W. Synlett 2001, 1364.
38. Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry 1995, 6, 2487.
39. 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.
40. (a) Saha, B.; Uchida, T.; Katsuki, T. Tetrahedron: Asymmetry 2003, 14, 823.
41. (b) Saha, B.; Uchida, T.; Katsuki, T. Chem. Lett. 2002, 846.
42. (c) Saha, B.; Uchida, T.; Katsuki, T. Synlett 2001, 114.
43. (d) Uchida, T.; Saha, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 2521.
44. Munslow, I. J.; Gillespie, K. M.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 1638.
45. 2(salen) = bis(salicylidene)-(1R,2R)-cyclo-hexanediamine.
46. Liang, J.-L.; Yu, X.-Q.; Che, C.-M. Chem. Commun. 2002, 124.
47. Yao, X.; Qiu, M.; Lü, W.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2001, 12, 197.
48. (a) Nishiyama, H.; Aoki, K.; Itoh, H.; Iwamura, T.; Sakata, N.; Kurihara, O.; Motoyama, Y. Chem. Lett. 1996, 1071.
49. (b) Park, S.-B.; Sakata, N.; Nishiyama, H. Chem. Eur. J. 1996, 2, 303.
50. Smith, D. A.; Reynolds, D. N.; Woo, L. K. J. Am. Chem. Soc. 1993, 115, 2511.
51. Lee, H. M.; Bianchini, C.; Jia, G.; Barbaro, P. Organometallics 1999, 18, 1961.
52. Ariel, S.; Dolphin, D.; Domazetis, G.; James, B. R.; Leung, T. W.; Rettig, S. J.; Trotter, J.; Williams, G. M. Can. J. Chem. 1984, 62, 755.
53. (a) Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Masciocchi, N.; Sironi, A.; Cenini, S. Inorg. Chem. 2005, 44, 2039.
54. (b) Khalil, M. M. H.; Aboaly, M. M.; Ramadan, R. M. Spectrochim. Acta, Part A 2005, 61, 157.
55. (c) Li, Y.; Chan, P. W. H.; Zhu, N.; Che, C.-M.; Kwong, H.-L. Organometallics 2004, 23, 54.
56. (d) Li, Y.; Huang, J.-S.; Xu, G.-B.; Zhu, N.; Zhou, Z.-Y.; Che, C.-M.; Wong, K.-Y. Chem. Eur. J. 2004, 10, 3486.
57. (e) Thangadurai, T. D.; Anitha, D.; Natarajan, K. Synth. React. Inorg. Met.-Org. Chem. 2002, 32, 1329.
58. (f) Flower, K. R.; Howard, V. J.; Pritchard, R. G.; Warren, J. E. Organometallics 2002, 21, 1184.
59. (g) Zhou, X.-G.; Huang, J.-S.; Ko, P.-H.; Cheung, K.-K.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1999, 3303.
60. (h) Klose, A.; Solari, E.; Floriani, C.; Geremia, S.; Randaccio, L. Angew. Chem., Int. Ed. 1998, 37, 148.
61. (i) Galardon, E.; Le Maux, P.; Toupet, L.; Simonneaux, G. Organometallics 1998, 17, 565.
62. (j) Slebodnick, C.; Seok, W. K.; Kim, K.; Ibers, J. A. Inorg. Chim. Acta 1996, 243, 57.
63. (k) Bonnet, J. J.; Eaton, S. S.; Eaton, G. R.; Holm, R. H.; Ibers, J. A. J. Am. Chem. Soc. 1973, 95, 2141.
64. Wong, C.-Y.; Che, C.-M.; Chan, M.C. W.; Leung, K.-H.; Phillips, D. L.; Zhu, N. J. Am. Chem. Soc. 2004, 126, 2501.
65. Mu, X. H.; Kadish, K. M. Langmuir 1990, 6, 51.
66. Scharbert, B.; Zeisberger, E.; Paulus, E. J. Organomet. Chem. 1995, 493, 143.
67. Karvembu, R.; Hemalatha, S.; Prabhakaran, R.; Natarajan, K. Inorg. Chem. Commun. 2003, 6, 486.
68. CCDC 252437-252439, 270753, 277479, 281163, and 281164 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or frqm the CCDC, 12 Union Road, Cambridge CB2 IEZ, U.K.; fax, +44 1223 336033; e-mail, deposit@ccdc.cam.ac.uk).
69. Serron, S. A.; Haar, C. M.; Nolan, S. P.; Brammer, L. Organometallics 1997, 16, 5120.
70. Omura, K.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Commun. 2004, 2060.
71. Kawai, M.; Yuge, H.; Miyamoto, T. K. Acta Crystallogr., Sect. C 2002, 58, M581.
72. (a) Miller, J. A.; Jin, W.; Nguyen, S. B. T. Angew. Chem., Int. Ed. 2002, 41, 2953.
73. (b) Miller, J. A.; Hennessy, E. J.; Marshall, W. J.; Scialdone, M. A.; Nguyen, S. B. T. J. Org. Chem. 2003, 68, 7884.
74. Stork, G.; Ficini, J. J. Am. Chem. Soc. 1961, 83, 4678.
75. (a) Xia, Q.-H.; Ge, H.-Q.; Ye, C.-P.; Liu, Z.-M.; Su, K.-X. Chem. Rev. 2005, 105, 1603.
76. (b) McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563.
77. Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Baker, W. R.; Condon, S. L.; deLara, E.; Rosenberg, S. H.; Spina, K. P.; Stein, H. H.; Cohen, J.; Kleinen, H. D. J. Med. Chem. 1992, 35, 1710.
78. (a) Zhang, J.; Liang, J.-L.; Sun, X.-R.; Zhou, H.-B.; Zhu, N.-Y.; Zhou, Z.-Y.; Chan, P. W. H.; Che, C.-M. Inorg. Chem. 2005, 44, 3942.
79. (b) Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072.
80. (c) Zhou, C.-Y.; Chan, P. W. H.; Yu, W.-Y.; Che, C.-M. Synthesis 2003, 9, 1403.
81. (d) Zhang, J.-L.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 8733.
82. (e) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M. Chem. Commun. 2003, 1362, 3052.
83. (f) Lai, T.-S.; Kwong, H.-L.; Che, C.-M. Tetrahedron: Asymmetry 2003, 14, 837.
84. (g) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M.; You, X.-Z. J. Am. Chem. Soc. 2002, 124, 13185.
85. (h) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M. J. Am. Chem. Soc. 2001, 123, 4843.
86. (i) Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mak, T. C. W. Chem. Commun. 1997, 1205.
87. Woo, L. K.; Smith, D. A. Organometallics 1992, 11, 2344.
88. (a) Katsuki, T. Synlett 2003, 281.
89. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
90. (c) Katsuki, T. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; p 287.
91. (d) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; p 607.
92. (e) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 2, p 113.
93. 3)2], see refs 11 and 12 and: (a) Sun, W.; Kühn, F. E. Appl. Catal, A: Gen. 2005, 285, 163.
94. (b) Bhowon, M. G.; Wah, H. L. K.; Narain, R. Polyhedron 1999, 18, 341.
95. SHELXL97: Sheldrick, G. M. SHELX97: Programs for Crystal Structure Analysis (Release 97-2); University of Göttingen, Göttingen, Germany, 1997.
96. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Carter, C. W., Sweet, R. M., Jr., Eds.; Academic Press: New York, 1997; Vol. 276, Macromolecular Crystallography, Part A, p 307.
97. SHELXS97: Sheldrick, G. M. SHELX97: Programs for Crystal Structure Analysis (Release 97-2); University of Göttingen, Göttingen, Germany, 1997.