Ruthenium-catalyzed highly efficient intramolecular olefin coupling of α,ω-dienes. Facile and regioselective synthesis of exo- methylenecyclopentanes

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2178-2179

  Yamamoto, Yoshihiko ^a   Ohkoshi, Naoki ^a   Kameda, Mitsutosi ^a   Itoh, Kenji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOPENTANE DERIVATIVE; HETEROCYCLIC COMPOUND; METHYLENECYCLOPENTANE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ORGANIC CHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0033515599     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982467m     Document Type: Article

References (41)

1. For a review of carbocyclizations, see: Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. (a) Broene, R. D. In Comprehensive Organometallic Chemistry II; Hegedua, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 323.
3. (b) Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 99.
4. (c) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 24, 124.
5. (a) Takacs, J. M. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1995; Vol. 12, p 9.
6. (b) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
7. (c) Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
8. (a) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
9. (b) Molander, G. A.; Knight, E. E. J. Org. Chem. 1998, 63, 7009.
10. Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
11. Widenhoefer, R. A.; DeCali, M. A. J. Am. Chem. Soc. 1998, 120, 3805.
12. (a) Waymouth, R. M.; Knight, K. S. J. Am. Chem. Soc. 1991, 113, 6268.
13. (b) Shaughnessy, K. H.; Waymouth, R. M. J. Am. Chem. Soc. 1995, 117, 5873.
14. (c) Yamaura, Y.; Hyakutake, M.; Mori, M. J. Am. Chem. Soc. 1997, 119, 7615.
15. Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404.
16. (a) Bright, A.; Malone, J. F.; Nicholson, J. K.; Powell, J.; Shaw, B. L. Chem. Commun. 1971, 712.
17. (b) Schmitz, E.; Urban, R.; Heuck, U.; Zimmermann, G.; Gründemann, E. J. Prakt. Chem. 1976, 318, 185.
18. (c) Schmitz, E.; Heuck, U.; Habisch, D. J. Prakt. Chem. 1976, 318, 471.
19. (d) Bodoganovic, B. Adv. Organomet. Chem. 1979, 17, 105.
20. (e) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1979, 669.
21. (f) Grigg, R.; Mitchell, T. R. B.; Ramasubbu, A. J. Chem. Soc., Chem. Commun. 1980, 27.
22. (g) Grigg, R.; Malone, J. F.; Mitchell, T. R. B.; Ramasubbu, A.; Scott, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 1745.
23. (h) Chritoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715.
24. (i) Thiele, S.; Erker, G. Chem. Ber./Rec. 1997, 130, 201.
25. (j) Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007.
26. (k) Heumann, A.; Moukhliss, M. Synlett 1998, 1211.
27. For related intramolecular ene-allene couplings, see: (a) Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1988, 110, 5231.
28. (b) Trost, B. M., Matsuda, K. J. Am. Chem. Soc. 1988, 110, 5233.
29. For related intramolecular ene-diene couplings, see: (a) Takacs, J. M.; Anderson, L. G. J. Am. Chem. Soc. 1987, 109, 2200.
30. (b) Takacs, J. M.; Anderson, L. G.; Creswell, M. W.; Takacs, B. E. Tetrahedron Lett. 1987, 28, 5627.
31. (c) Takacs, J. M.; Newsome, P. W.; Kuehn, C.; Takusagawa, F. Tetrahedron 1990, 46, 5507.
32. (d) Takacs, B. E.; Takacs, J. M. Tetrahedron Lett. 1990, 31, 2865.
33. (e) Takacs, J. M.; Myoung, Y. C. Tetrahedron Lett. 1992, 33, 317.
34. (f) Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219.
35. For related intramolecular diene-diene couplings, see: Takacs, J. M.; Clement, F.; Zhu, J.; Chandramouli, S. V.; Gong, X. J. Am. Chem. Soc. 1997, 119, 5804.
36. (a) Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
37. (b) Dérien, S.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 2551.
38. (c) Dérien, S.; Jan, D.; Dixneuf, P. H. Tetrahedron 1996, 52, 5511.
39. (d) Yamamoto, Y.; Kitahara, H.; Hattori, R.; Itoh, K. Organometallics 1998, 17, 1910.
40. (e) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem., in press.
41. Bennet, M. A.; Wilkinson, G. Chem. Ind. (London) 1959, 1516. This complex is also commercially available.