Ruthenium-catalyzed intramolecular [5 + 2] cycloadditions [5]

Journal of the American Chemical Society

Volumn 122, Issue 10, 2000, Pages 2379-2380

  Trost, Barry M ^a   Toste, F Dean ^a   Shen, Hong ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; ALKYNE; RUTHENIUM;

CATALYSIS; CHEMICAL STRUCTURE; LETTER; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; TEMPERATURE;

EID: 0034654486     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993400z     Document Type: Letter

References (20)

1. Review: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 39, 2805.
2. For a recent general review of ruthenium-catalyzed reactions, see: Murahashi, S.-I.; Takaya, H.; Naota, T. Chem. Rev. 1998, 98, 2599.
3. Trost, B. M; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. For preparation of 1, see Gill, T. P.; Mann, K. R. Organometallics 1982, 1, 485.
4. Trost, B. M; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739. For preparation of 1, see Gill, T. P.; Mann, K. R. Organometallics 1982, 1, 485.
5. For examples of ruthenium-catalyzed intermolecular reactions, see: (a) Trost, B. M. Indolese, A. Muller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. (b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988. (e) For a review, see: Trost, B. M. Chem. Ber. 1996, 129, 1313.
6. For examples of ruthenium-catalyzed intermolecular reactions, see: (a) Trost, B. M. Indolese, A. Muller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. (b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988. (e) For a review, see: Trost, B. M. Chem. Ber. 1996, 129, 1313.
7. For examples of ruthenium-catalyzed intermolecular reactions, see: (a) Trost, B. M. Indolese, A. Muller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. (b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988. (e) For a review, see: Trost, B. M. Chem. Ber. 1996, 129, 1313.
8. For examples of ruthenium-catalyzed intermolecular reactions, see: (a) Trost, B. M. Indolese, A. Muller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. (b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988. (e) For a review, see: Trost, B. M. Chem. Ber. 1996, 129, 1313.
9. For examples of ruthenium-catalyzed intermolecular reactions, see: (a) Trost, B. M. Indolese, A. Muller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615. (b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988. (e) For a review, see: Trost, B. M. Chem. Ber. 1996, 129, 1313.
10. For reviews of transition metal catalyzed cycloadditions see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; p1-49.
11. For reviews of transition metal catalyzed cycloadditions see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; p1-49.
12. For reviews of transition metal catalyzed cycloadditions see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (b) Dell, C. P. Contemp. Org. Synth. 1997, 4, 87. Wender, P. A.; Love, J. A. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; p1-49.
13. (a) Alkynes: Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
14. (b) Alkenes: Wender, P. A. Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940.
15. (c) Allenes: Wender, P. A.; Glorious, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137.
16. (c) Allenes: Wender, P. A.; Glorious, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett. 1999, 1, 137.
17. d) For an intermolecular example, see: Binger, P.; Wedermann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 113.
18. 6a An alternative Rh catalyst was recently reported to circumvent this problem. Wender, P. A.; Sperandio, D. A. J. Org. Chem. 1998, 63, 4164.
19. 6b
20. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.