Scandium-bipyridine-catalyzed, enantioselective alcoholysis of meso-epoxides

European Journal of Organic Chemistry

Volumn , Issue 14, 2007, Pages 2318-2327

  Tschöp, Andreas ^a   Marx, Andreas ^a,b   Sreekanth, Anakallil R ^a,c   Schneider, Christoph ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^c UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

Alcohols; Asymmetric catalysis; Desymmetrization; Epoxide; Scandium bipyridine

Indexed keywords

EID: 34250688196     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601101     Document Type: Article

References (73)

1. Most recent and comprehensive reviews: a) C. Schneider, Synthesis 2006, 3919-3944;
2. b) I. M. Pastor, M. Yus, Curr. Org. Chem. 2005, 9, 1-29.
3. a) H. Yamashita, Bull. Chem. Soc. Jpn. 1988, 61, 1213-1220;
4. b) M. Hayashi, K. Kohmura, N. Oguni, Synlett 1991, 774-776;
5. c) W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768-2769;
6. d) L. E. Martinez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897-5898;
7. e) R. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10780-10781;
8. f) H. Adolfsson, C. Moberg, Tetrahedron: Asymmetry 1995, 6, 2023-2031.
9. a) X. L. Hou, J. Wu, L. X. Dai, L. J. Xia, M. H. Tang, Tetrahedron: Asymmetry 1998, 9, 1747-1752;
10. b) S. Sagawa, H. Abe, Y. Hase, T. Inaba, J. Org. Chem. 1999, 64, 4962-4965;
11. c) A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 58, 75-82;
12. d) S. Azoulay, K. Manabe, S. Kobayashi, Org Lett. 2005, 7, 4593-4595;
13. 3-bipyridine-catalyzed aminolysis of meso-epoxides see: C. Ogawa, S. Azoulay, S. Kobayashi, Heterocycles 2005, 66, 201-206;
14. f) F. Carree, R. Gil, J. Collin, Org. Lett. 2005, 7, 1023-1026;
15. F. Carree, R. Gil, J. Collin, Tetrahedron Lett. 2004, 45, 7749-7751;
16. g) R. V. Jasra, R. I. Kureshy, S. Singh, N. H. Khan, S. H. R. Abdi, E. Suresh, Eur. J. Org. Chem. 2006, 1303-1309; ;
17. 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.
18. E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773-776.
19. 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.
20. a) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784;
21. b) M. H. Wu, E. N. Jacobsen, J. Org. Chem. 1998, 63, 5252-5254;
22. c) S. Y. Ko, K. B. Sharpless, J. Org. Chem. 1986, 51, 5413-5415;
23. d) J. Wu, X. L. Hou, L. X. Dai, L. J. Xia, M. H. Tang, Tetrahedron: Asymmetry 1998, 9, 3431-3436.
24. M. Yang, C. Zhu, F. Yuan, Y. Huang, Y. Pan, Org. Lett. 2005, 7, 1927-1930.
25. a) W. A. Nugent, J. Am. Chem. Soc. 1998, 120, 7139-7140;
26. b) S. E. Denmark, P. A. Barsanti, K. T. Wong, R. A. Stavenger, J. Org. Chem. 1998, 63, 2428-2429;
27. c) B. Tao, M. M. C. Lo, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 353-354;
28. d) M. Nakaijama, M. Saito, M. Uemura, S. Hashimoto, Tetrahedron Lett. 2002, 43, 8827-8829;
29. e) E. Tokuoka, S. Kotani, H. Matsunaga, T. Ishizuka, S. Hashimoto, M. Nakaijama, Tetrahedron: Asymmetry 2005, 16, 2391-2392;
30. f) S. Bruns, G. Haufe, J. Fluorine Chem. 2000, 104, 247-254;
31. g) G. Haufe, S. Bruns, Adv. Synth. Catal. 2002, 344, 165-171.
32. a) 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;
33. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
34. b) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782-1785;
35. Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707;
36. c) S. E. Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001-1004;
37. d) C. Zhu, F. Yuan, W. Gu, Y. Pan, Chem. Commun. 2003, 692-693.
38. a) M. Mizuno, M. Kanai, A. Iida, K. Tomioka, Tetrahedron: Asymmetry 1996, 7, 2483-2484;
39. b) A. Alexakis, E. Vrancken, P. Mangeney, Synlett 1998, 1165-1167;
40. E. Vrancken, A. Alexakis, P. Mangeney, Eur. J. Org. Chem. 2005, 1354-1366;
41. c) N. Oguni, Y. Miyagi, K. Itoh, Tetrahedron Lett. 1998, 39, 9023-9026;
42. d) C. Zhu, M. Yang, J. Sun, Y. Zhu, Y. Pan, Synlett 2004, 465-468;
43. e) F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Org. Lett. 2000, 2, 933-936;
44. f) F. Bertozzi, P. Crotti, F. Del Moro, V. Di Bussolo, F. Macchia, M. Pineschi, Eur. J. Org. Chem. 2003, 1264-1270;
45. g) F. Del Moro, P. Crotti, V. Di Bussolo, F. Macchia, M. Pineschi, Org. Lett. 2003, 5, 1971-1974;
46. h) F. Bertozzi, P. Crotti, F. Del Moro, B. L. Feringa, F. Macchia, M. Pineschi, Chem. Commun. 2001, 2606-2607.
47. a) C. Schneider, A. R. Sreekanth, E. Mai, Angew. Chem. 2004, 116, 5809-5812;
48. Angew. Chem. Int. Ed. 2004, 43, 5691-5694;
49. for some recent nonenantioselective metal-catalyzed alcohol additions to epoxides see; b) P. R. Lihkar, M. P. Kumar, A. K. Bandyopadhyay, Synlett 2001, 836-838;
50. c) J. Barluenga, H. Vazquez-Villa, A. Ballesteros, J. M. Gonzalez, Org. Lett. 2002, 4, 2817-2819;
51. d) A. Berkessel, E. Ashkenazi, M. R. M. Andreae, Appl. Catal, A 2003, 27;
52. e) B. M. Choudary, K. Jyothi, S. Mahdi, M. L. Kantam, Synlett 2004, 231-234.
53. For the first synthesis and application of bipyridine 2 in asymmetric catalysis see a) C. Bolm, M. Zehnder, D. Bur, Angew. Chem. 1990, 102, 206-208;
54. Angew. Chem. Int. Ed. Engl. 1990, 29, 191-193;
55. b) C. Bolm, M. Ewald, M. Zehnder, M. A. Neuburger, Chem. Ber. 1992, 125, 453-458.
56. Reviews: a) S. Kobayashi, Eur. J. Org. Chem. 1999, 15-27;
57. b) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev. 2002, 102, 2227-2302.
58. S. E. Denmark, Y. Fan, J. Am. Chem. Soc. 2002, 124, 4233-4235.
59. Excellent review about nonlinear effects: H. Kagan, C. Girard, Angew. Chem. 1998, 110, 3088-3127;
60. Angew. Chem. Int. Ed 1998, 37, 2922-2959.
61. A. J. Manusco, D. Swern, Synthesis 1981, 165-184.
62. a) R. Johansson, B. Samuelsson, J. Chem. Soc., Perkin Trans. 1 1984, 2371;
63. b) G. I. Georg, P. M. Mashava, E. Akgün, M. W. Milstead, Tetrahedron Lett. 1991, 32, 3151-3154.
64. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236-12237.
65. H. Shechter, B. K. Ravi Shankar, Tetrahedron Lett. 1982, 23, 2277-2280.
66. L. Zhao, B. Han, Z. Huang, M. Miller, H. Huang, D. Malashock, Z. Zhu, A. Milan, D. E. Robertson, D. P. Weiner, M. J. Burk, J. Am. Chem. Soc. 2004, 126, 11156-11157.
67. K. Tomioka, A. Iida, M. Kanai, M. Mizuno, Tetrahedron 1997, 53, 10699-10708.
68. J. Aube, C. J. Mossman, S. Dickey, Tetrahedron 1992, 48, 9819-9826.
69. S. Kobayashi, M. Shiro, S. Nagayama, S. Ishikawa, K. Manabe, T. Hamada, J. Am. Chem. Soc. 2003, 125, 2989-2996.
70. K. B. Sharpless, Z.-M. Wang, J. Org. Chem. 1994, 59, 8302-8303.
71. H. Hönig, P. Seufer-Wasserthal, Synthesis 1990, 1137-1140.
72. S. C. Jha, N. N. Joshi, J. Org. Chem. 2002, 67, 3897-3899.
73. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, Synthesis 2005, 2176-2182.