A Ru Catalyzed Addition of Alkenes to Alkynes

Journal of the American Chemical Society

Volumn 117, Issue 2, 1995, Pages 615-623

  Trost, Barry M ^a   Indolese, Adriano F ^a   Müller, Thomas J J ^a   Treptow, Björe ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000369431     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00107a005     Document Type: Article

References (44)

1. Trost, B. M. Science 1991, 254, 1471.
2. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557.
3. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476;.
4. Snider, B. B. Acc. Chem. Res. 1980, 13, 426.
5. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reaction; Springer-Verlag: Berlin, 1984.
6. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1–28.
7. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527–561.
8. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, University Science Books: Mill Valley, 1987; pp 509–12, 868–77.
9. For reviews, see: Shore, N. E. Chem. Rev. 1988, 88, 1081.
10. Winter, M. J. In The Chemistry of the Metal-Carbon Bond. Carbon-Carbon Bond Formation Using Organometallic Compounds; Hartley, F. R.; Patai, S., Eds.; Wiley: Chichester, 1985; Vol. 3, Chapter 5.
11. Bird, C. W. Transition Metal Intermediates in Organic Synthesis; Logos: London, Academic Press: New York, 1967; Vol. 1, Chapter 1.
12. Trost, B. M. Dyker, G.; Kulawiec, R. J. J. Am. Chem. Soc. 1990, 112, 7809.
13. Trost, B. M.; Kulawiec, R. J. J. Am. Chem. Soc. 1992, 114, 5579.
14. Trost, B. M.; Flygare, J. A. J. Am. Chem. Soc. 1992, 114, 5476.
15. Trost, B. M.; Kulawiec, R. J.; Hammes, A. Tetrahedron Lett. 1993, 34, 587.
16. Trost, B. M.; Flygare, J. A. J. Org. Chem. 1994, 59, 1078.
17. Trost, B. M.; Flygare, J. A. Tetrahedron Lett. B 1994, 35, 4059.
18. Bruce, M. I. Chem. Rev. 1991, 191, 197.
19. Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; John Wiley & Sons: New York, 1988.
20. Bruce, M. I.; Swincer, G. A. Adv. Organomet. Chem. 1983, 22, 59.
21. Albers, M. O.; Robinson, D. J.; Shaver, A.; Singleton, E. Organometallics 1986, 5, 2199.
22. For a review, see: Davies, S. G.; McNally, J. P.; Smalridge, A. J. Adv. Organomet. Chem. 1990, 30, 1.
23. For Cp* equivalent, see: Masuda, K.; Ohkita, H.; Kurumatani, S.; Itoh, K. Organomet. 1993, 12, 2221.
24. Urbanos, F.; Halcrow, M. A.; Femandez-Baeza, J.; Dahan, F.; Labroue, D.; Chaudret, B. J. Am. Chem. Soc. 1993, 115, 3484.
25. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402.
26. Trost, B. M.; Kulawiec, R. J. Tetrahedron Lett. 1991, 32, 3039; J. Am. Chem. Soc. 1993, 115, 2027.
27. For use of other Ru catalysts, see: Backvall, J. E.; U. Andreasson Tetrahedron Lett. 1993, 34, 5459.
28. McGrath, D. V.; Grubbs, R. H. Organometallics 1994, 13, 224.
29. Lin, Y.; Zhu, X.; Zhou, Y. J. Organomet. Chem. 1992, 429, 269.
30. For a preliminary report of a portion of this work, see: Trost, B. M.; Indolese, A. J. Am. Chem. Soc. 1993, 115, 4361.
31. Indolese, A. F. unpublished results from these laboratories.
32. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233;
33. Arthur, T.; Stephenson, T. A. J. Organomet. Chem. 1981, 208, 369.
34. For a review, see: le Bozec, H.; Touchard, D.; Dixneuf, P. H. Adv. Organomet. Chem. 1989, 29, 163.
35. Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831.
36. Tsuji, Y.; Mukai, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1989, 369, C51;
37. Kondo, T.; Mukai, T.; Watanabe, Y. J. Org. Chem. 1991, 56, 487.
38. For other reactions involving a ruthenacyclopentene intermediate, see; Mitsudo, T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanabe, Y.; Takegami, Y. J. Org. Chem. 1979, 44, 4492.
39. Mitsudo, T.; Zhang, S.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598.
40. Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831.
41. Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
42. Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
43. Cetini, G.; Gambino, O.; Sappa, E.; Valle, M. J. Organomet. Chem. 1969, 17, 437.
44. Burt, R.; Cooke, M.; Green, M. J. Chem. Soc. A 1970, 2981.