Ruthenium-catalyzed cycloisomerizations of 1,6- and 1,7-enynes [2]

Journal of the American Chemical Society

Volumn 122, Issue 4, 2000, Pages 714-715

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

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; RUTHENIUM;

CATALYSIS; ISOMERISM; LETTER;

EID: 0033952688     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993401r     Document Type: Letter

References (21)

1. Trost, B. M. Science 1991, 254, 1471; Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
2. Trost, B. M. Science 1991, 254, 1471; Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. For reviews see: Trost, B. M.; Krische, M. J. Synlett 1998, 1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. For reviews see: Trost, B. M.; Krische, M. J. Synlett 1998, 1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
5. (a) Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. (b) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. (c) Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 6268. (d) Co (mediated): Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y. Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 58, 5911.
6. (a) Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. (b) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. (c) Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 6268. (d) Co (mediated): Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y. Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 58, 5911.
7. (a) Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. (b) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. (c) Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 6268. (d) Co (mediated): Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y. Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 58, 5911.
8. (a) Pd: Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255 and references therein. (b) Ti: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976. (c) Ni-Cr: Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 6268. (d) Co (mediated): Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. K.; Cheung, Y. Y.; Fu, Z.; Shao, B.; Scott, J. L. Tetrahedron Lett. 1998, 58, 5911.
9. (a) Trost, B. M.; Indolese, A. F.; Muller, T. J. J. Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
10. (b) Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888.
11. Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739.
12. For alternative Ru-catalyzed transformations of 1,6-enynes see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9725. (b) Nishida, M.; Adachi, N. Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (c) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. For a general review of Ru-catalyzed reactions see: (d) Murahashi, S.-I.; Takaya, H.; Naota, T. Chem. Rev. 1998, 98, 2599.
13. For alternative Ru-catalyzed transformations of 1,6-enynes see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9725. (b) Nishida, M.; Adachi, N. Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (c) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. For a general review of Ru-catalyzed reactions see: (d) Murahashi, S.-I.; Takaya, H.; Naota, T. Chem. Rev. 1998, 98, 2599.
14. For alternative Ru-catalyzed transformations of 1,6-enynes see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9725. (b) Nishida, M.; Adachi, N. Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (c) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. For a general review of Ru-catalyzed reactions see: (d) Murahashi, S.-I.; Takaya, H.; Naota, T. Chem. Rev. 1998, 98, 2599.
15. For alternative Ru-catalyzed transformations of 1,6-enynes see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9725. (b) Nishida, M.; Adachi, N. Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (c) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. For a general review of Ru-catalyzed reactions see: (d) Murahashi, S.-I.; Takaya, H.; Naota, T. Chem. Rev. 1998, 98, 2599.
16. For cycloisomerization leading to; Furans: Trost, B. M.; Edstrom, E. D.; Carter-Petillo, M. B. J. Org. Chem. 1989, 54, 4489. Pyrrolidines: Trost, B. M.; Chen, S.-F. J. Am. Chem. Soc. 1986, 108, 6053 and ref 3b.
17. For cycloisomerization leading to; Furans: Trost, B. M.; Edstrom, E. D.; Carter-Petillo, M. B. J. Org. Chem. 1989, 54, 4489. Pyrrolidines: Trost, B. M.; Chen, S.-F. J. Am. Chem. Soc. 1986, 108, 6053 and ref 3b.
18. Attempts to utilize a 1,8-enyne resulted in only 20% conversion to the seven-membered ring.
19. Trost, B. M.; Lautens, M.; Chan, C.; Jebaratnam, D. J.; Mueller, T. J. Am. Chem. Soc. 1991, 111, 636.
20. Trost, B. M.; Chung, J. Y. L. J. Am. Chem. Soc. 1985, 107, 4586.
21. Trost, B. M.; Phan, L. T. Tetrahedron Lett. 1993, 34, 4735.