Rhodium(I)-catalyzed intramolecular [5+2] cycloaddition reactions of alkynes and allenylcyclopropanes: Construction of bicyclo[5.4.0]undecatrienes and bicyclo[5.5.0]dodecatrienes

Angewandte Chemie - International Edition

Volumn 49, Issue 12, 2010, Pages 2206-2210

  Inagaki, Fuyuhiko ^a   Sugikubo, Katsuya ^a   Miyashita, Yusuke ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Allenes; Bicyclic compounds; Cycloaddition; Cyclopropanes; Rhodium

Indexed keywords

ALKADIENE; ALKYNE; BICYCLO COMPOUND; CYCLOPROPANE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

ALKADIENES; ALKYNES; BICYCLO COMPOUNDS; CATALYSIS; CYCLOPROPANES; RHODIUM;

EID: 77953951452     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906994     Document Type: Article

References (56)

1. For recent reviews, see: a) C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051-3060;
2. b) M. Rubin, M. Marina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179;
3. c) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321-347;
4. d) M. Rubina, V. Gevorgyan, Tetrahedron 2004, 60, 3129-3159;
5. e) O. G. Kulin- kovich, Chem. Rev. 2003, 103, 2597-2632.
6. For selected leading references, see : a) D. F. Taber, K. Kanai, Q. Jiang, G. Bui, J. Am. Chem. Soc. 2000, 122, 6807-6808;
7. b) B. M. Trost, H.C. Shen, Org. Lett. 2000, 2, 2523-2525;
8. c) B. M. Trost, F. D. Toste, H. Shen, J. Am. Chem. Soc. 2000, 122, 2379-2380;
9. d) P. A. Wender, G. G. Gamber, R. D. Hubbard, L. Zhang, J. Am. Chem. Soc. 2002, 124, 2876-2877;
10. e) Y. Wang, J. Wang, J. Su, F. Huang, L. Jiao, Y Liang, D. Yang, S. Zhang, P. A. Wender, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 10060-10061;
11. f) T. Matsuda, T. Tsuboi, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12596-12597;
12. g) M. A. A. Walczak, P. Wipf, J. Am. Chem. Soc. 2008, 130, 6924-6925;
13. h) S. Y Kim, S. I. Lee, S. Y. Choi, Y. K. Chung, Angew. Chem. 2008, 120, 4992-4995;
14. Angew. Chem. Int. Ed. 2008, 47, 4914-4917;
15. i) L. Jiao, Z.-X. Yu, J. Am. Chem. Soc. 2008, 130, 7178-7179;
16. j) P. A. Evans, P.A. Inglesby, J. Am. Chem. Soc. 2008, 130, 12838-12839;
17. k) X. Fan, M.-X. Tang, L.G. Zhou, Y. Q. Tu, Z.-X. Yu, Tetrahedron Lett. 2009, 50, 155157;
18. l) Y Zhang, Z. Chen, Y Xiao, J. Zhang, Chem. Eur. J. 2009, 15, 5208-5211.
19. a) P. A. Wender, H. Takahashi, B. Witulski, J. Am. Chem. Soc. 1995, 117, 4720-4721;
20. b) P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, N. Pleuss, Tetrahedron 1998, 54, 7203-7220;
21. c) P. A. Wender, D. Sperandio, J. Org. Chem. 1998, 63, 4164-4165;
22. d) P. A. Wender, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1998, 120, 1940-1941;
23. e) P. A. Wender, F. Glorius, C. O. Husfeld, E. Langkopf, J. A. Love, J. Am. Chem. Soc. 1999, 121, 5348-5349;
24. f) P. A. Wender, M. Fuji, C. O. Husfeld, J. A. Love, Org. Lett. 1999, 1, 137-139;
25. g) P. A. Wender, A. J. Dyckman, C. O. Husfeld, D. Kadereit, J. A. Love, H. Rieck, J. Am. Chem. Soc. 1999, 121, 10442-10443;
26. h) P. A. Wender, L. Zhang, Org. Lett. 2000, 2, 2323-2326;
27. i) P. A. Wender, F. C. Bi, M. A. Brodney, F. Gosselin, Org. Lett. 2001, 3, 2105-2108;
28. j) P. A. Wender, T. I. Williams, Angew. Chem. 2002, 114, 4732-4735;
29. Angew. Chem. Int. Ed. 2002, 41, 4550-4553;
30. k) F. J. Gómez, N. E. Kamber, N. M. Deschamps, A. P. Cole, P. A. Wender, R. M. Waymouth, Organometallics 2007, 26, 4541-4545.
31. 1-catalyzed asymmetric cycloaddition of vinylcyclopropanes with alkynes, see: a) P. A. Wender, L. O. Haustedt, J. Lim, J. A. Love, T. J. Williams, J.-Y. Yoon, J. Am. Chem. Soc. 2006, 128, 6302-6303;
32. b) R. Shintani, H. Nakatsu, K. Takatsu, T. Hayashi, Chem. Eur. J. 2009, 15, 8692-8694.
33. For mechanistic considerations, see: a) Z.-X. Yu, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 9154-9155;
34. b) Z.-X. Yu, P. H.-Y. Cheong, P. Liu, C. Y. Legault, P. A. Wender, K. N. Houk, J. Am. Chem. Soc. 2008, 130, 2378-2379;
35. c) P. Liu, H.-Y. Cheong, Z.-X. Yu, P. A. Wender, K. N. Houk, Angew. Chem. 2008, 120, 4003-4005;
36. Angew. Chem. Int. Ed. 2008, 47, 3939-3941.
37. a) Y Owada, T. Matsuda, N. Iwasawa, Tetrahedron 1997, 53, 11069-11086;
38. b) M. Hayashi, T. Ohmatsu, Y.-P. Meng, K. Saigo, Angew. Chem. 1998, 110, 877 -879;
39. Angew. Chem. Int. Ed. 1998, 37, 837-839;
40. c) M. Murakami, K. Itami, M. Ubukata, I. Tsuji, Y. Ito, J. Org. Chem. 1998, 63, 4-5;
41. d) M. Schmittel, A. A. Mahajan, G. Bucher, J. W Bats, J. Org. Chem. 2007, 72, 2166-2173;
42. e) K. Hiroi, F. Kato, T. Oguchi, S. Saito, T. Sone, Tetrahedron Lett. 2008, 49, 3567-3569.
43. a) C. Mukai, I. Nomura, K. Yamanishi, M. Hanaoka, Org. Lett. 2002, 4, 1755-1758;
44. b) C. Mukai, I. Nomura, S. Kitagaki, J. Org. Chem. 2003, 68, 1376-1385;
45. c) C. Mukai, F. Inagaki, T. Yoshida, S. Kitagaki, Tetrahedron Lett. 2004, 45, 4117-4121;
46. d) C. Mukai, F. Inagaki, T. Yoshida, K. Yoshitani, Y. Hara, S. Kitagaki, J. Org. Chem. 2005, 70, 7159-7171;
47. e) C. Mukai, T. Hirose, S. Teramoto, S. Kitagaki, Tetrahedron 2005, 61, 10983 -10994;
48. f) F. Inagaki, C. Mukai, Org. Lett. 2006, 8, 1217-1220;
49. g) F. Inagaki, T. Kawamura, C. Mukai, Tetrahedron 2007, 63, 5154-5160;
50. h) F. Inagaki, S. Narita, T. Hasegawa, S. Kitagaki, C Mukai, Angew. Chem. 2009, 121, 2041-2045;
51. Angew. Chem. Int. Ed. 2009, 48, 2007-2011.
52. 1 catalyst for the next investigation.
53. b was observed.
54. M. E. Jung, G. Piizzi, Chem. Rev. 2005, 105, 1735-1766.
55. 2] under 10 atm of CO for 1 h.
56. 2] catalyst. Figure Presented