GaCl3-catalyzed allenyne cycloisomerizations to allenenes

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 7120-7123

  Lee, Sang Ick ^a   Sim, So Hee ^a   Kim, Soo Min ^a   Kim, Kwang ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; SUBSTITUTION REACTIONS; TOLUENE;

ALLENIC TERMINAL CARBON; ALLENYNES; CYCLOISOMERIZATIONS;

OLEFINS;

ALLENE DERIVATIVE; ALLENENE DERIVATIVE; GALLIUM CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; ISOMERIZATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33750451929     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061318y     Document Type: Article

References (53)

1. For reviews, see: (a) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
2. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
3. (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
5. (a) Brummond, K. M.; You, L. F. Tetrahedron 2005, 61, 6180.
6. (b) Gupta, A. K.; Rhim, C. Y.; Oh, C. H. Tetrahedron Lett. 2005, 46, 2247.
7. (c) Oh, C. H.; Park, D. I.; Jung, S. H.; Reddy, V. R.; Gupta, A. K.; Kim, Y. M. Synlett 2005, 2092.
8. (d) Kumareswaran, R.; Shin, S.; Gallou, I.; RajanBabu, T. V. J. Org. Chem. 2004, 69, 7157.
9. (e) Shibata, T.; Kadowaki, S.; Takagi, K. Organometallics 2004, 23, 4116.
10. (f) Mukai, C.; Inagaki, F.; Yoshida, T.; Kitagaki, S. Tetrahedron Lett. 2004, 45, 4117.
11. (g) Oh, C. H.; Jung, S. H.; Park, D. I.; Choi, J. H. Tetrahedron Lett. 2004, 45, 2499.
12. (h) Oh, C. H.; Jung, S. H.; Rhim, C. Y. Tetrahedron Lett. 2001, 42, 8669.
13. (i) Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295.
14. (a) Mukai, C.; Hirose, T.; Teramoto, S.; Kitagaki, S. Tetrahedron 2005, 61, 10983.
15. (b) Brummond, K. M.; Curran, D. P.; Mitasev, B.; Fischer, S. J. Org. Chem. 2005, 70, 1745.
16. (c) Cao, H.; Van Ornum, S. G.; Deschamps, J.; Flippen-Anderson, J.; Laib, F.; Cook, J. M. J. Am. Chem. Soc. 2005, 127, 933.
17. (d) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2004, 3377.
18. (e) Brummond, K. M.; Gao, D. Org. Lett. 2003, 5, 3491.
19. (e) Brummond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156.
20. (f) Brummond, K. M.; Chen, H. F.; Fisher, K. D.; Kerekes, A. D.; Rickards, B.; Sill, P. C.; Geib, S. J. Org. Lett. 2002, 4, 1931.
21. (f) Mukai, C.; Nomura, I.; Yamanishi, K.; Hanaoka, M. Org. Lett. 2002, 4, 1755.
22. (g) Brummond, K. M.; Lu, J. L.; Petersen, J. J. Am. Chem. Soc. 2000, 122, 4915.
23. (h) Brummond, K. M.; Lu, J. L. J. Am. Chem. Soc. 1999, 121, 5087.
24. (i) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931.
25. (j) Kent, J. L.; Wan, H. H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407.
26. For reviews, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
27. (b) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
28. (c) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
29. (d) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
30. (e) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
31. For Au- and Pt-catalyzed enyne cycloisomerizations, see: (f) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431.
32. (g) Nieto-Oberhuber, C.; Löpez, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6179.
33. (h) Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
34. (i) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
35. (j) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511.
36. (k) Oi, S.; Tsukamoto, L; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704.
37. (a) Matsuda, T.; Kadowaki, S.; Goya, T.; Murakami, M. Synlett 2006, 575.
38. (b) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408.
39. (a) Mamane, V.; Hannen, P.; Fûrstner, A. Chem. Eur. J. 2004, 10, 4556.
40. (b) Chatani, N.; Oshita, M.; Tobisu, M.; Ishii, Y.; Murai, S. J. Am. Chem. Soc. 2003, 125, 7812.
41. (c) Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294.
42. (d) Fûrstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
43. (e) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414.
44. (a) Peppers, B. P.; Diver, S. T. J. Am. Chem. Soc. 2004, 126, 9524.
45. (b) Schmidt, B. Angew. Chem., Int. Ed. 2003, 42, 4996.
46. (c) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.
47. (d) Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
48. (e) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
49. Nieto-Oberhuber, C.; Muñoz, M. P.; López, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 1677.
50. Miyanohana, Y.; Chatani, N. Org. Lett. 2006, 8, 2155.
51. 4 was active in the cycloisomerization of some enyne substrates. Lee, S. I.; Baek, J. Y.; Chung, Y. K. Manuscript in preparation.
52. Murakami, M.; Kadowaki, S.; Matsuda, T. Org. Lett. 2005, 7, 3953.
53. One of the referees suggested an alternative, path "b", as a possible reaction path.