HOTf-catalyzed rearrangement of methylenecyclopropane aryl and alkyl alcohols

European Journal of Organic Chemistry

Volumn , Issue 21, 2010, Pages 4106-4110

  Tang, Xiang Ying ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alcohols; Aromaticity; Ring expansion; Small ring systems

Indexed keywords

EID: 77954740195     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000509     Document Type: Article

References (70)

1. For recent reviews on. MCPs, see: a) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92;
2. b) A. de Meijere, S. I. Kozhushkov, A. F. Khlebnikov, Top. Curr. Chem. 2000, 207, 89-147;
3. c) P. Binger, P. Wedemann, S. I. Kozhushkov, A. de Meijere, Eur. J. Org. Chem. 1998, 113-119;
4. d) A. de Meijere, S. I. A. Kozhushkov, Eur. J. Org. Chem. 2000, 3809-3822;
5. e) I. Nakamura, Y. Yamamoto, Adv. Synth. Catal. 2002, 344, 111129;
6. f) A. Brandi, S. Cicchi, F. M. Cordero, A. Goti, Chem. Rev. 2003, 103, 1213-1270;
7. g) E. Nakamura, S. Yamago, Acc. Chem. Res. 2002, 35, 867-877;
8. h) L.-X. Shao, M. Shi, Curr. Org. Chem. 2007, 11, 1135-1137;
9. i) M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179;
10. j) S. Yamago, E. Nakamura, Org. React. 2002, 61, 1-217;
11. k) A. de Meijere, S. I. Kozhushkov, T. Spath, M. von Seebach, S. Lohr, H. Nuske, T. Pohomann, M. Es-Sayed, S. Brase, Pure Appl. Chem. 2000, 72, 1745-1756.
12. For selected examples on the reactions of MCPs, see: a) B. Hu, S. Y. Xing, Z. W. Wang, Org. Lett. 2008, 10, 5481-5484;
13. b) M. Shi, L.-P. Liu, J. Tang, Org. Lett. 2006, 8, 4043-4046;
14. c) M. Shi, B. Xu, J.-W. Huang, Org. Lett. 2004, 6, 1175-1178;
15. d) X. Huang, Y. Yang, Org. Lett. 2007, 9, 1667-1670;
16. e) M. Lautens, W. Han, J. H. Liu, J. Am. Chem. Soc. 2003, 125, 4028-4029;
17. f) M. Lautens, Y. Ren, J. Am. Chem. Soc. 1996, 118, 10668-10669;
18. g) L. Yu, J. D. Meng, L. Xia, R. Guo, J. Org. Chem. 2009, 74, 5087-5089;
19. h) S. Ma, J. Zhang, Angew. Chem. 2003, 115, 193-197;
20. Angew. Chem. Int. Ed. 2003, 42, 183-187;
21. i) S. Ma, L. Lu, J. Zhang, J. Am. Chem. Soc. 2004, 126, 9645-9660>;
22. j) L. Lu, G. Chen, S. Ma, Org. Lett, 2006, 8, 835-838;
23. k) M. E. Scott, M. Lautens, J. Org. Chem, 2008, 73, 8154-8162;
24. C. Taillier, M. Lautens, Org. Lett, 2007, 9, 591-593;
25. m) E. Smolensky, M. Kapon, M. S. Eisen, Organometallics 2007, 26, 4510-4527;
26. n) V. V. Diev, T. Q. Tung, A. P. Molchanov, Eur. J. Org. Chem. 2009, 525-530;
27. o) B. Hu, J. L. Zhu, S. Y. Xing, J. Fang, D. Du, Z. W. Wang, Chem. Eur. J. 2009, 15, 324-327;
28. p) V. Bagutski, A. de Meijere, Adv. Synth. Catal. 2007, 349, 1247-1255;
29. q) X.-C. Hang, Q.-Y. Chen, J.-C. Xiao, Eur. J. Org. Chem. 2008, 1101-1106;
30. r) I. Nakamura, B. H. Oh, S. Saito, Y Yamamoto, Angew. Chem. 2001, 113, 1338-1340;
31. Angew. Chem. Int. Ed. 2001, 40, 1298-1300;
32. s) T. Kurahashi, A. de Meijere, Angew. Chem. 2005, 117, 8039-8096;
33. Angew. Chem. Int. Ed. 2005, 44, 7881-7884;
34. t) X. Huang, H. Zhou, Org. Lett. 2002, 4, 4419-4422.
35. For the Lewis acid mediated cycloaddition of MCPs with activated ketone or aldehyde, see: a) M. Shi, B. Xu, Tetrahedron Lett. 2003, 44, 3839-3842;
36. 2-mediated ring expansions of methylenecyclopropylamides and imides, see: b) M. Lautens, W. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316;
37. 4, see: c) H. Monti, D. Rizzotto, G. Leandri, Tetrahedron 1998, 54, 6725-6738;
38. for the cycloaddition of gem-dialkoxy-substituted MCPs with, aldehydes and imines upon heating, see: d) S. Yamago, E. Nakamura, J. Org. Chem. 1990, 55, 5553-5555;
39. e) S. Yamago, M. Yanagawa, E. Nakamura, Chem. Lett. 1999, 879-880;
40. for some related Lewis acid or Brønsted acid mediated reactions of MCPs, see: f) G. L. N. Peron, J. Kitteringham, J. D. Kilburn, Tetrahedron Lett. 1999, 40, 3045-3048;
41. g) K. Miura, M. Takasumi, T. Hondo, A. Hosomi, H. Saito, Tetrahedron Lett. 1997, 38, 4587-4590;
42. h) G. L. N. Peron, J. Kitteringham, J. D. Kilburn, Tetrahedron Lett. 2000, 41, 1615-1618;
43. i) L. Patient, M. B. Berry, J. D. Kilburn, Tetrahedron Lett. 2003, 44, 1015-1017;
44. j) G. Peron, D. Norton, J. Kitteringham, J. D. Kilburn, Tetrahedron Lett. 2001, 42, 347-349;
45. k) L. Patient, M. B. Berry, S. J. Coles, M. B. Hursthouse, J. D. Kilburn, Chem. Commun. 2003, 2552-2553;
46. A. I. Siriwardana, I. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2003, 44, 4547-4550;
47. m) S. Rajamaki, J. D. Kilburn, Chem. Commun. 2005, 1637-1639;
48. n) M. Suginome, T. Matsuda, Y. Ito, J. Am. Chem. Soc. 2000, 122, 11015;
49. M. Suginome, T Matsuda, T. Yoshimoto, Y. Ito, Org. Lett. 1999, 1, 1567-1569;
50. p) M. Suginome, Y. Ohmori, Y. Ito, Synlett 1999, 1567-1568;
51. q) M. Suginome, T. Matsuda, H. Nakamura, Y. Ito, Tetrahedron 1999, 55, 8787-8800.
52. For some of the Lewis acid or Bronsted acid mediated transformations of MCPs in this laboratory, see: a) M. Shi, B. Xu, Org. Lett. 2002, 4, 2145-2148;
53. b) J.-W. Huang, M. Shi, Tetrahedron 2004, 60, 2057-2062;
54. c) L.-X. Shao, M. Shi, Eur. J. Org. Chem. 2004, 426-430;
55. d) Y. Chen, M. Shi, J Org. Chem. 2004, 69, 426-431;
56. e) L.-X. Shao, M. Shi, Adv. Synth. Catal. 2003, 345, 963-966;
57. f) M. Shi, Y. Chen, J. Fluorine Chem. 2003, 122, 219-227;
58. g) J.-W. Huang, M. Shi, Tetrahedron Lett. 2003, 44, 9343-9347;
59. h) M. Shi, Y. Chen, B. Xu, J. Tang, Green Chem. 2003, 5, 85-88;
60. i) B. Xu, M. Shi, Org. Lett. 2003, 5, 1415-1418;
61. j) M. Shi, L.-X. Shao, B. Xu, Org. Lett. 2003, 5, 579-582;
62. k) M. Shi, Y. Chen, B. Xu, J. Tang, Tetrahedron Lett. 2002, 43, 8019-8024;
63. J.-W. Huang, M. Shi, Synlett 2004, 2343-2346;
64. m) L.-X. Shao, J.-W. Huang, M. Shi, Tetrahedron 2004, 60, 11895-11901;
65. n) E. B. Verina, K. N. Sedenkova, I. S. Borisov, Y. K. Grishin, T. S. Kuznetsova, N. S. Zefirov, Tetrahedron 2009, 65, 5693-5701.
66. L.-F. Yao, Y Wei, M. Shi, J. Org. Chem. 2009, 74, 9466-9469.
67. P. Cordier, C. Aubert, M. Malacria, E. Lacote, V. Gandon, Angew. Chem. 2009, 121, 8913-8916;
68. Angew. Chem. Int. Ed. 2009, 48, 8757-8760.
69. This is a known compound and its spectroscopic data are consistent with those reported in the literature: G. W Kabalka, Y.H. Ju, Z.-Z. Wu, J. Org. Chem. 2003, 68, 7915-7917.
70. T. M. Khomenko, I. Yu. Bagryanskaya, Yu. V. Gatilov, D. V. Korchagina, V. P. Gatilova, Zh. V. Dubovenko, V. A. Barkhash, Zh. Org. Khim. 1985, 21, 677-678.