Asymmetric meso-epoxide ring-opening with trimethylsilyl cyanide promoted by chiral binuclear complexes of titanium. Dichotomy of C-C versus C-N bond formation

Advanced Synthesis and Catalysis

Volumn 351, Issue 18, 2009, Pages 3157-3167

  Belokon, Yuri N ^a   Chusov, Denis ^a   Peregudov, Alexander S ^a   Yashkina, Lidia V ^a   Timofeeva, Galina I ^a   Maleev, Victor I ^a   North, Michael ^b   Kagan, Henri B ^c  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

^c UNIVERSITÉ PARIS SUD   (France)

Author keywords

Asymmetric ring opening; Binuclear catalysts; Meso epoxides; N C dichotomy; Trimethylsilyl cyanide

Indexed keywords

EID: 73349117787     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900523     Document Type: Article

References (63)

1. C. Schneider, Synthesis 2006, 3919-3944.
2. S. E. Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001-1004.
3. I. M. Pastor, M. Yus, Current Organic Chemistry, 2005, 9, 1-29;
4. M. Pineschi, Eur. J. Org. Chem. 2006, 4979-4988.
5. H. Yamashita, Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220;
6. M. Hayashi, K. Kohmura, N. Oguni, Synlett., 1991, 774-776;
7. W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768-2769;
8. B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656-6666;
9. L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898;
10. K. B. Hansen, J. L. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10924-10925;
11. R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780-10781;
12. H. Adolfsson, C. Moberg, Tetrahedron: Asymmetry 1995, 6, 2023-2031;
13. J. L. Leighton, E. N. Jacobsen, J. Org. Chem. 1996, 61, 389-390;
14. J. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420-7421.
15. S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260;
16. C. Schneider, A. R. Sreekanth, E. Mai, Angew. Chem. 2004, 116, 5809-5812;
17. Angew. Chem. Int. Ed. 2004, 43, 5691-5694.
18. C. A. G. M. Weijers, Tetrahedron: Asymmetry 1997, 8, 639-647;
19. L. Zhao, B. Han, Z. Huang, M. Miller, H. Huang, D. S. Malashock, Z. Zhu, A. Milan, D. E. Robertson, D. P. Weiner, M. J. Burk, J. Am. Chem. Soc. 2004, 126, 11156-11157;
20. J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688.
21. H. Yamashita, T. Mukaiyama, Chem. Lett. 1985, 14, 1643-1646;
22. T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784;
23. M. H. Wu, E. N. Jacobsen, J. Org. Chem, 1998, 63, 5252-5254;
24. J. Wu, X. L. Hou, L. X. Dai, L. J. Xia, M. H. Tang, Tetrahedron: Asymmetry 1998, 9, 3431-3436;
25. Y.-J. Chen, C. Chen, Tetrahedron: Asymmetry 2007, 18, 1313-1319.
26. M. Yang, C. Zhu, F. Yuan, Y. Huang, Y. Pan, Org. Lett. 2005, 7, 1927-1930.
27. K. Arai, M. M. Salter, Y. Yamashita, S. Kobayashi, Angew. Chem. 2007, 119, 973-975;
28. Angew. Chem. Int. Ed. 2007, 46, 955-957;
29. R. I. Kureshy, S. Singh, N. H. Khan, S. H. R. Abdi, E. Suresh, R. V. Jasra, Eur. J. Org. Chem. 2006, 1303-1309;
30. F. Carree, R. Gil, J. Collin, Org. Lett. 2005, 7, 1023-1026;
31. X. L. Hou, J. Wu, L. X. Dai, L. J. Xia, M. H. Tang, Tetrahedron: Asymmetry 1998, 9, 1747-1752;
32. S. Sagawa, H. Abe, Y. Hase, T. Inaba, J. Org. Chem. 1999, 64, 4962-4965;
33. A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 58, 75-82;
34. S. Azoulay, K. Manabe, S. Kobayashi, Org. Lett. 2005, 7, 4593-4595;
35. C. Ogawa, S. Azoulay, S. Kobayashi, Heterocycles 2005, 66, 201-206;
36. F. Carree, R. Gil, J. Collin, Tetrahedron Lett. 2004, 45, 7749-7751;
37. R. I. Kureshy, S. Singh, N. Khan, S. H. R. Abdi, S. Agrawal, V. J. Mayani, R. V. Jasra, Tetrahedron Lett. 2006, 47, 5277-5279.
38. W. A. Nugent, J. Am. Chem. Soc. 1998, 120, 7139-7140;
39. S. E. Denmark, P. A. Barsanti, K. T. Wong, R. A. Stavenger, J. Org. Chem. 1998, 63, 2428-2429;
40. B. Tao, M. M.. C. Lo, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 353-354;
41. C. E. Garrett, G. C. Fu, J. Org. Chem. 1997, 62, 4534-4535;
42. M. Nakaijama, M. Saito, M. Uemura, S. Hashimoto, Tetrahedron Lett. 2002, 43, 8827-8829;
43. E. Tokuoka, S. Kotani, H. Matsunaga, T. Ishizuka, S. Hashimoto, M. Nakaijama, Tetrahedron: Asymmetry 2005, 16, 2391-2392;
44. S. Bruns, G. Haufe, J. Fluorine Chem. 2000, 104, 247-254;
45. G. Haufe, S. Bruns, Adv. Synth. Catal. 2002, 344, 165-171.
46. B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779;
47. Angew. Chem. Int. Ed. Engl. 1996, 35, 15, 1668-1671;
48. K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782-1785;
49. Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707, 1703-1707.
50. Y. N. Belokon, D. Chusov, D. A. Borkin, L. V. Yashkina, A. V. Dmitriev, D. Katayev, M. North, Tetrahedron: Asymmetry 2006, 17, 2328-2333;
51. Y. N. Belokon, D. Chusov, T. V. Skrupskaya, D. A. Borkin, L. A. Yashkina, K. A. Lysenko, M. M. Ilyin, T. V. Strelkova, G. I. Timofeeva, A. S. Peregudov, M. North, Russ. Chem. Bull. 2008, 57, 1981-1988.
52. B. Saha, M.-H. Lin, T. V. RajanBabu, J. Org. Chem. 2007, 72, 8648-8655.
53. K. Imi, N. Yanagihara, K. Utimoto, J. Org. Chem. 1987, 52, 1013-1016.
54. Y. N. Belokon, S. Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Khrustalev, V. S. Larichev, M. A. Moscalenko, M. North, C. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, L. V. Yashkina, J. Am. Chem. Soc. 1999, 121, 3968-3973;
55. Y. N. Belokon, V. I. Maleev, M. North, D. L. Usanov, Chem. Commun. 2006, 4614-4616;
56. Y. N. Belokon, W. Clegg, R. W. Harrington, V. I. Maleev, M. North, M. O. Pujol, D. L. Usanov, C. Young, Chem. Eur. J. 2009, 15, 2148-2165.
57. P. G. Gassman, T. L. Guggenheim, J. Am. Chem. Soc. 1982, 104, 5849-5850.
58. F. G. Glansdorp, G. L. Thomas, J. K. Lee, J. M. Dutton, G. P. C. Salmond, M. Welch, D. R. Spring, Org. Biomol. Chem. 2004, 2, 3329-3336;
59. A. Chaterjee, M. Sasikumar, N. N. Joshi, Synth. Commun. 2007, 37, 1727-1733;
60. A. Nishida, F. Shirato, M. Nakagawa, Tetrahedron: Asymmetry 2000, 11, 3789-3805.
61. C. Zhu, F. Yuan, W. Gu, Y. Pan, Chem. Commun. 2003, 692-693;
62. F. Yuan, C. Zhu, J. Sun, Y. Liu, Y. Pan, J. Organomet. Chem. 2003, 682, 102-107.
63. Y. Belokon, E. Ishibashi, H. Nomura, M. North, Chem. Commun. 2006, 1775-1777.