Skeletal reorganization of enynes catalyzed by InCl3

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2155-2158

  Miyanohana, Yuhei ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33744758661     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060606d     Document Type: Article

References (57)

1. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
2. Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
3. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
4. Añorbe, L.; Domínguez, G.; Pérez-Castells, J. Chem. Eur. J. 2004, 10, 4938-4943.
5. Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328-2334.
6. Two transformations, enyne metathesis and skeletal reorganization, should be differentiated, although both reactions give 1-vinylcycloalkenes. Catalysts which can be used and the reaction mechanism are totally different. Enyne metathesis appears to proceed through a metal alkylidene mechansim, and only type I products are obtained. In addition, enyne metathesis involves an intermolecular process (see: Lloyd-Jones, G. C.; Margue, R. G.; de Vries, J. G. Angew. Chem., Int. Ed. 2005, 44, 7442-7447).
7. (a) Ru(II): Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049-6050.
8. (b) Pt(II): Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901-903.
9. (c) Ir(I): Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433-4436.
10. (d) Ga(III): Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295.
11. Pd: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636-1638.
12. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850-1852.
13. Pt: (c) Trost, B. M.; Chang, V. K. Synthesis 1993, 824-832.
14. (d) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305-8314.
15. (e) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810.
16. (f) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785-6786.
17. (g) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869.
18. (h) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704-3709.
19. (i) Oh, C. H.; Bang, S. Y.; Rhim, C. Y. Bull. Korean Chem. Soc. 2003, 24, 887.
20. (j) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655.
21. (k) Bajracharya, G. B.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2005, 70, 892-897.
22. Au: (l) Nieto-Oberhuber, C.; Munoz, M. P.; Bunuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-2406.
23. (m) Mézailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133-4136.
24. (n) Nieto-Oberhuber, C.; Muñoz, M. P.; Lopez, S.; Jiménez-Núñez, E.; Nevado, C.; Herrero-Gómez, E.; Raducan, M.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 1677-1693. Ru:
25. (o) Madhushaw, R. J.; Lo, C.-Y.; Hwang, C.-W.; Su, M.-D.; Shen, H.-C.; Pal, S.; Shaikh, I. R.; Liu, R.-S. J. Am. Chem. Soc. 2004, 126, 15560-15565.
26. (a) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431-436.
27. (b) Soriano, E.; Ballesteros, P.; Marco-Contelles, J. Organometallics 2005, 24, 3172-3181.
28. (c) Nieto-Oberhuber, C.; López, S.; Muñoz, M. P.; Cárdenas, D. J.; Buñuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146.
29. (d) Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2005, 70, 9345-9353. See also refs 3d and 4f.
30. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105.
31. Mainetti, E.; Mouries, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 4l, 2132-2135.
32. Nieto-Oberhuber, C.; Lopez, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178-6179.
33. See also: Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085-1087.
34. Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183-2184.
35. (a) Nevado, C.; Echavarren, A. M. Synthesis 2005, 167-182.
36. (b) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913-4918.
37. (c) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
38. (d) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414-1417.
39. (e) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563.
40. (f) Mamane, V.; Hannen, P.; Fürstner, A. Chem. Eur. J. 2004, 10, 4556-4575.
41. (g) Nevado, C.; Echavarren, A. M. Chem. Eur. J. 2005, 11, 3155-3164.
42. See also: Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553-11554.
43. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654-8655.
44. Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656-8657.
45. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546-2547.
46. Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858-10859.
47. Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802-5803.
48. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962-6963.
49. Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244-8245.
50. Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002-13003.
51. Tsuchimoto, T.; Hatanaka, K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454-2455. See also ref 6f.
52. For a characterization of 1-vinylcyclopentenes, see ref 3.
53. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967.
54. Kim, H.; Lee, C. J. Am. Chem. Soc. 2005, 127, 10180-10181. See also refs 41 and 4n.
55. Oi reported that the Pt cation-catalyzed reaction of 4 gives a 5:1 mixture of 5 and the usual skeletal reorganization product. Tsukamoto, I.; Oi, S.; Inoue, Y. 46th Symposium on Organometallic Chemistry; Kinki Chemical Society, Japan, 1999; Abstract PB245.
56. Echavarren proposed that a 1,2-shift from the gold carbene complex related to 26 into the complex similar to 31 takes place. See ref 5c.
57. The direct conversion of 27 to type II' is an alternative route.