Ruthenium-catalyzed cyclodimerization of allenynes

Organometallics

Volumn 28, Issue 3, 2009, Pages 669-671

  Saito, Nozomi ^a   Tanaka, Yuki ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; RUTHENIUM; RUTHENIUM COMPOUNDS;

ALKYLIDENE; ALLENYNES; CYCLODIMERIZATION; DOUBLE BONDS; FIVE-MEMBERED RINGS; FOUR-MEMBERED RINGS; HIGH YIELDS; PENTACYCLIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

EID: 61849170693     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om801181a     Document Type: Article

References (48)

1. Mitsudo, T.; Kokuryo, K.; Takegami, Y. J. Chem. Soc, Chem. Commun. 1976, 722.
2. For reviews, see: (a) Naota, T.; Takaya, H.; Murahashi, S. Chem. Rev. 1998, 98, 2599.
3. (b) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
4. (c) Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem., Int. Ed. 2005, 44, 6630.
5. (d) Ruthenium in Organic Synthesis; Murahashi, S., Ed.; Wiley-VCH: New York, 2002.
6. (e) Ruthenium Catalysts and Fine Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer-Verlag: Berlin, Heidelberg, 2004; Top. Organomet. Chem. Vol. 11.
7. For representative examples, see: (a) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
8. (b) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801 For similar reactions catalyzed by Ru-NHC catalysts, see:
9. (c) Ackermann, L.; Bruneau, C.; Dixneuf, P. H. Synlett 2001, 397.
10. (d) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728.
11. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714.
12. (f) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
13. (g) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
14. (h) Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379.
15. (a) Mori, M.; Saito, N.; Tanaka, D.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 5606.
16. (b) Tanaka, D.; Sato, Y.; Mori, M. Organometallics 2006, 25, 799.
17. (c) Tanaka, D.; Sato, Y.; Mori, M. J. Am. Chem. Soc. 2007, 129, 7730.
18. (a) Oh, C. H.; Gupta, A. K.; Park, D. I.; Kim, N. Chem. Commun. 2005, 5670.
19. (b) Bai, T.; Xue, P.; Zhang, Li.; Ma, S.; Jia, G. Chem. Commun. 2008, 2929. For Ru-catalyzed intermolecular reactions of aliene and other multiple bonds, see:
20. (c) Yamaguchi, M.; Kido, Y.; Omata, K.; Hirama, M. Synlett 1995, 1181.
21. (d) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 4068. For Ru-catalyzed intramolecular reactions of allenynes, see:
22. (e) Vovard-Le Bray, C.; Dérien, S.; Dixneuf, P. H.; Murakami, M. Synlett 2008, 193.
23. For representative examples of cyclization via type I or II metallacycles formed from allenynes and transition metals except for ruthenium, see: (a) Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
24. (b) Aubert, C.; Llerena, D.; Malacria, M. Tetrahedron Lett. 1994, 35, 2341.
25. (c) Llerena, D.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1996, 37, 7027.
26. (d) Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295.
27. (e) Ahmar, M.; Locatelli, C.; Colombier, D.; Cazes, B. Tetrahedron Lett. 1997, 38, 5281.
28. (f) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931.
29. (g) Pagenkopf, B. L.; Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Synthesis 2000, 1009.
30. (h) Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73.
31. (i) Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186.
32. (j) Shen, Q.; Hammond, G. B. J. Am. Chem. Soc. 2002, 124, 6534.
33. (k) Brummond, K. M.; Mitasev, B. Org. Lett. 2004, 6, 2245.
34. (l) Mukai, C.; Inagaki, F.; Yoshida, T.; Yoshitani, K.; Hara, Y.; Kitagaki, S. J. Org. Chem. 2005, 70, 7159.
35. (m) Jiang, X.; Ma, S. J. Am. Chem. Soc. 2007, 129, 11600.
36. The structures of all dimeric products were strongly supported by both high-resolution mass spectroscopy and various 2D NMR spectroscopie methods (COSY, NOESY, HMQC, and HMBC). The stereochemistries of the products were assigned by analogy with the spectral data of 5g, whose stereochemistry was unambiguously determined by X-ray crystallographic analysis. Crystallographic data for 5g have been deposited at the Cambridge Crystallographic Data Center (CCDC).
37. For examples of cyclobutene synthesis by ruthenium-catalyzed [2 + 2] cycloaddition, see: (a) Mitsudo, T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanabe, Y.; Takegami, Y. J. Org. Chem. 1979, 44, 4492.
38. (b) Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
39. (c) Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043.
40. (d) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310.
41. (e) Jordan, R. W.; Tam, W. Org. Lett. 2000, 2, 3031.
42. (f) Le Paih, J.; Dérien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2001, 40, 2912.
43. (g) Alvarez, P.; Gimeno, J.; Lastra, E.; García-Granda, S.; Van der Maelen, J. F.; Bassetti, M. Organometallics 2001, 20, 3762.
44. (h) Tenaglia, A.; Giordano, L. Synlett 2003, 2333.
45. (i) Le Paih, J.; Dérien, S.; Demerseman, B.; Bruneau, C.; Dixneuf, P. H.; Toupet, L.; Dazinger, G.; Kirchner, K. Chem. Eur. J. 2005, 11, 1312.
46. See also ref 1.
47. For construction of polycyclobutane frameworks via rutheniumcatalyzed [2 + 2] cycloaddition of cyclobutene and DMAD, see: Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Am. Chem. Soc. 1994, 116, 3645.
48. For other examples of ruthenium-catalyzed dimerization of strained alkenes, see: Mitsudo, T.; Suzuki, T.; Zhang, S.-W.; Imai, D.; Fujita, K.; Manabe, T.; Shiotsuki, M.; Watanabe, Y.; Wada, K.; Kondo, T. J. Am. Chem. Soc. 1999, 121, 1839.