Versatile domino rearrangement of diphenylhomobenzoquinone epoxides induced by CF 3SO 3H

European Journal of Organic Chemistry

Volumn , Issue 21, 2012, Pages 3916-3919

  Asahara, Haruyasu ^a   Matsui, Satoshi ^a   Masuda, Yoshiro ^a   Ikuma, Naohiko ^a   Oshima, Takumi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Decarbonylation; Domino reactions; Epoxides; Pseudopericyclic reaction; Rearrangement

Indexed keywords

EID: 84863919983     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201200455     Document Type: Article

References (67)

1. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137
2. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
3. L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
4. P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206.
5. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis Wiley, New York, 2006.
6. T. L. Ho, Tandem Reactions in Organic Synthesis Wiley, New York, 1992.
7. N. Okamoto, K. Takeda, R. Yanada, J. Org. Chem. 2010, 75, 7615-7625.
8. J. Huang, X. Huang, B. Liu, Org. Biomol. Chem. 2010, 8, 2697-2699.
9. M. Presset, Y. Coquerel, J. Rodriguez, Org. Lett. 2010, 12, 4212-4215.
10. T. R. Ramadhar, J. Kawakami, J. A. Lough, R. A. Batey, Org. Lett. 2010, 12, 4446-4449.
11. N. Shimada, S. Nakamura, M. Anada, M. Shiro, S. Hashimoto, Chem. Lett. 2009, 38, 488-489.
12. L. Liu, J. Zhang, Angew. Chem. 2009, 121, 6209
13. Angew. Chem. Int. Ed. 2009, 48, 6093-6096.
14. N. Toselli, D. Martieu, M. Achard, A. Tenaglia, G. Buono, J. Org. Chem. 2009, 74, 3783-3791.
15. Z. Elkhayat, I. Safir, P. Retailleau, S. Arseniyadis, Org. Lett. 2007, 9, 4841-4844.
16. P. Hickford, J. R. Baker, I. Bruce, K. I. Booker-Milbum, Org. Lett. 2007, 9, 4681-4684.
17. J. He, K. Tchabanenko, R. M. Adlington, A. R. Cowley, J. E. Baldwin, Eur. J. Org. Chem. 2006, 4003-4013.
18. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
19. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
20. H. Pellissier, Tetrahedron 2006, 62, 1619-1665.
21. H. Pellissier, Tetrahedron 2006, 62, 2143-2173.
22. B. Augustyns, N. Maulide, I. E. Markõ, Tetrahedron Lett. 2005, 46, 3895-3899.
23. H. M. L. Davies, X. Dai, J. Org. Chem. 2005, 70, 6680-6684.
24. L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805.
25. R. M. A. Lavigne, M. Riou, M. Girardin, L. Morency, L. Barriault, Org. Lett. 2005, 7, 5921-5923.
26. L. E. Overmann, L. D. Pennington, J. Org. Chem. 2003, 68, 7143-7157.
27. T. Hattori, Y. Suzuki, Y. Ito, D. Hotta, S. Miyano, Tetrahedron 2002, 58, 5215-5223.
28. G. S. Viswanathan, C.-J. Li, Synlett 2002, 1553-1555.
29. V. M. Dong, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 2448-2449.
30. K. Kokubo, H. Yamagichi, T. Kawamoto, T. Oshima, J. Am. Chem. Soc. 2002, 124, 8912-8921.
31. T. Koizumi, K. Harada, H. Asahara, E. Mochizuki, K. Kokubo, T. Oshima, J. Org. Chem. 2005, 70, 8364-8371.
32. K. Kokubo, T. Koizumi, T. Oshima, J. Org. Chem. 2005, 70, 7776-7779.
33. T. Koizumi, K. Harada, E. Mochizuki, K. Kokubo, T. Oshima, Org. Lett. 2004, 6, 4081-4084.
34. T. Koizumi, E. Mochizuki, K. Kokubo, T. Oshima, J. Org. Chem. 2004, 69, 4577-4585.
35. K. Kokubo, T. Koizumi, H. Yamagichi, T. Oshima, Tetrahedron Lett. 2001, 42, 5025-5028.
36. H. Asahara, K. Saito, N. Ikuma, T. Oshima, J. Org. Chem. 2010, 75, 733-740.
37. H. Asahara, E. Kubo, K. Togaya, T. Koizumi, E. Mochizuki, T. Oshima, Org. Lett. 2007, 9, 3421-3424.
38. O. Khdour, E. B. Skibo, Org. Biomol. Chem. 2009, 7, 2140-2154.
39. T. Kumamoto, N. Tabe, K. Yamaguchi, H. Yagishita, H. Iwasa, T. Ishikawa, Tetrahedron 2001, 57, 2717-2728.
40. C.-P. Chuang, S.-F. Wang, Synlett 1996, 9, 829-830 and to 3-furanones 5, 6 see
41. E. M. Bunnelle, C. R. Smith, S. K. Lee, S. W. Singaram, A. J. Rhodes, R. Sarpong, Tetrahedron 2008, 64, 7008-7014.
42. C. M. Marson, E. Edaan, J. M. Morrell, S. J. Coles, M. B. Hursthouse, D. T. Davies, Chem. Commun. 2007, 2494-2496.
43. S. F. Kirsch, J. T. Binder, C. Liébert, H. Menz, Angew. Chem. 2006, 118, 6010
44. Angew. Chem. Int. Ed. 2006, 45, 5878-5880.
45. Y. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett. 2006, 8, 3445-3448.
46. Similar 1,2-shift of the alkyl groups to the acid-activated carbonyl functions is reported for cyclic α-hydoxyketones, see:, L. A. Paquette, J. E. Hofferberth, Org. React. 2003, 62, 477-567.
47. th ed., Wiley, New York, 2001, pp. 281-284.
48. E. Chamorro, J. Chem. Phys. 2003, 118, 8687-8698.
49. B. F. LeBlance, R. S. Sheridan, J. Am. Chem. Soc. 1985, 107, 4554-4555.
50. J. W. Bevan, A. C. Legon, J. Chem. Soc. Faraday Trans. 2 1973, 69, 902-925.
51. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, VCH, Weinheim, 1970.
52. S. Calvo-Losada, J. J. Q. Sánchez, J. Phys. Chem. A 2008, 112, 8164-8178.
53. S. Sakai, Theor. Chem. Acc. 2008, 120, 177-183.
54. K. Fukushima, H. Iwasaki, Heterocycles 2005, 65, 2605-2618.
55. K. Fukushima, H. Iwasaki, Bull. Chem. Soc. Jpn. 2004, 77, 1671-1679.
56. J. A. Ross, R. P. Seiders, D. M. Lemal, J. Am. Chem. Soc. 1976, 98, 4325-4327.
57. D. M. Birney, X. Xu, S. Ham, Angew. Chem. 1999, 111, 147
58. Angew. Chem. Int. Ed. 1999, 38, 189-193.
59. D. M. Birney, S. Ham, G. R. Unruh, J. Am. Chem. Soc. 1997, 119, 4509-4517.
60. D. Birney, J. Org. Chem. 1996, 61, 243-251.
61. D. M. Birney, P. E. Wagenseller, J. Am. Chem. Soc. 1994, 116, 6262-6270.
62. H. Asahara, E. Kubo, K. Togaya, T. Koizumi, E. Mochizuki, T. Oshima, Org. Lett. 2007, 9, 3421-3424.
63. R. D. Bach, G. J. Wolber, J. Am. Chem. Soc. 1984, 106, 1410-1415.
64. H. Iwamura, T. Sugawara, Y. Kawada, K. Tori, R. Muneyuki, R. Noyori, Tetrahedron Lett. 1979, 20, 3449-3452.
65. P. D. Mollere, K. N. Houk, J. Am. Chem. Soc. 1977, 99, 3226-3233.
66. J. R. Otero, E. M. C. Lago, J. M. H. Ramõn, A. P. P. Gallego, J. Org. Chem. 2003, 68, 8823-8830.
67. H.-X. Wei, C. Zhou, S. Ham, J. M. White, D. M. Birney, Org. Lett. 2004, 6, 4289-4292.