A ruthenium-catalyzed two-component addition to form 1,3-dienes

Journal of the American Chemical Society

Volumn 121, Issue 16, 1999, Pages 4068-4069

  Trost, Barry M ^a   Pinkerton, Anthony B ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; KETONE; RUTHENIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033611984     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990291f     Document Type: Article

References (24)

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2. Oppozer, W. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.1, pp 315-400. Roush, W. R. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.4, pp 513-550.
3. Oppozer, W. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.1, pp 315-400. Roush, W. R. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.4, pp 513-550.
4. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 1988.
5. For some recent Ru-catalyzed 1,3 diene syntheses, see: Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361. Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
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9. For some examples of Pd-catalyzed C-C bond formation at the central carbon of allenes, see: Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816. Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233. Larock, R. C.; Veraprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. Alper, H.; Hartstock, F. W.; Despeyroux, B. Chem. Commun. 1984, 905.
10. For some examples of Pd-catalyzed C-C bond formation at the central carbon of allenes, see: Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816. Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233. Larock, R. C.; Veraprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. Alper, H.; Hartstock, F. W.; Despeyroux, B. Chem. Commun. 1984, 905.
11. For some examples of Pd-catalyzed C-C bond formation at the central carbon of allenes, see: Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816. Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233. Larock, R. C.; Veraprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. Alper, H.; Hartstock, F. W.; Despeyroux, B. Chem. Commun. 1984, 905.
12. For some examples of Pd-catalyzed C-C bond formation at the central carbon of allenes, see: Trost, B. M.; Kottirsch, G. J. Am. Chem. Soc. 1990, 112, 2816. Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233. Larock, R. C.; Veraprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. Alper, H.; Hartstock, F. W.; Despeyroux, B. Chem. Commun. 1984, 905.
13. Gamez, P.; Ariente, C.; Goré, J.; Cazes, B. Tetrahedron 1998, 54, 14835. Ahmar, M.; Barieux, J. J.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 513. Larock, R. C.; Berrios-Pefia, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615. Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kirn, Y. S. Synlett 1993, 88. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
14. Gamez, P.; Ariente, C.; Goré, J.; Cazes, B. Tetrahedron 1998, 54, 14835. Ahmar, M.; Barieux, J. J.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 513. Larock, R. C.; Berrios-Pefia, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615. Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kirn, Y. S. Synlett 1993, 88. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
15. Gamez, P.; Ariente, C.; Goré, J.; Cazes, B. Tetrahedron 1998, 54, 14835. Ahmar, M.; Barieux, J. J.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 513. Larock, R. C.; Berrios-Pefia, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615. Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kirn, Y. S. Synlett 1993, 88. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
16. Gamez, P.; Ariente, C.; Goré, J.; Cazes, B. Tetrahedron 1998, 54, 14835. Ahmar, M.; Barieux, J. J.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 513. Larock, R. C.; Berrios-Pefia, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615. Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kirn, Y. S. Synlett 1993, 88. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
17. Gamez, P.; Ariente, C.; Goré, J.; Cazes, B. Tetrahedron 1998, 54, 14835. Ahmar, M.; Barieux, J. J.; Cazes, B.; Goré, J. Tetrahedron 1987, 43, 513. Larock, R. C.; Berrios-Pefia, N. G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615. Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, S. W.; Kirn, Y. S. Synlett 1993, 88. Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
18. For a Ru-catalyzed C-C bond formation at the central carbon of allenes, see: Yamaguchi, M.; Kido, Y.; Omata, K.; Hirama, M. Synlett 1995, 1181.
19. For examples of carbapalladation of alienes, see: Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Asao, N. Tetrahedron Lett. 1995, 36, 2811.
20. For examples of carbapalladation of alienes, see: Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. Yamamoto, Y.; Al-Masum, M.; Fujiwara, N.; Asao, N. Tetrahedron Lett. 1995, 36, 2811.
21. For a proposed hydropalladation mechanism, see: Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117-, 5156. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. J. Am. Chem. Soc. 1997, 36, 11750. Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831. Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453.
22. For a proposed hydropalladation mechanism, see: Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117-, 5156. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. J. Am. Chem. Soc. 1997, 36, 11750. Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831. Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453.
23. For a proposed hydropalladation mechanism, see: Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117-, 5156. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. J. Am. Chem. Soc. 1997, 36, 11750. Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831. Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453.
24. For a proposed hydropalladation mechanism, see: Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117-, 5156. Trost, B. M.; Michellys, P.-Y.; Gerusz, V. J. J. Am. Chem. Soc. 1997, 36, 11750. Yamamoto, Y.; Al-Masum, M.; Takeda, A. Chem. Commun. 1996, 831. Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453.