New three-component synthesis of 1,3-dienes employing nickel catalysis

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9310-9313

  Qi, Xin ^a   Montgomery, John ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; NICKEL;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 0032783952     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912810     Document Type: Article

References (26)

1. For recent reviews, see: (a) Oppolzer, W. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.1, pp 315-400. (b) 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.
2. For recent reviews, see: (a) Oppolzer, W. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 4.1, pp 315-400. (b) 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. For representative recent preparative methods, see: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 4068. (b) Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388. (c) Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361.
4. For representative recent preparative methods, see: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 4068. (b) Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388. (c) Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361.
5. For representative recent preparative methods, see: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 4068. (b) Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388. (c) Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361.
6. (a) Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911.
7. (b) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065.
8. (c) Seo, J.; Chui, H. M. P.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476.
9. For preparation of dienes via elimination of δ-hydroxy allylsilanes, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534. (b) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (c) Yamashita, K.; Sato, F. Tetrahedron Lett. 1996, 37, 7275. (d) Nativi, C.; Taddei, M.; Mann, A. Tetrahedron 1989, 45, 1131.
10. For preparation of dienes via elimination of δ-hydroxy allylsilanes, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534. (b) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (c) Yamashita, K.; Sato, F. Tetrahedron Lett. 1996, 37, 7275. (d) Nativi, C.; Taddei, M.; Mann, A. Tetrahedron 1989, 45, 1131.
11. For preparation of dienes via elimination of δ-hydroxy allylsilanes, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534. (b) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (c) Yamashita, K.; Sato, F. Tetrahedron Lett. 1996, 37, 7275. (d) Nativi, C.; Taddei, M.; Mann, A. Tetrahedron 1989, 45, 1131.
12. For preparation of dienes via elimination of δ-hydroxy allylsilanes, see: (a) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1984, 534. (b) Maeta, H.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5969. (c) Yamashita, K.; Sato, F. Tetrahedron Lett. 1996, 37, 7275. (d) Nativi, C.; Taddei, M.; Mann, A. Tetrahedron 1989, 45, 1131.
13. For alternative methods for preparing δ-hydroxy allylsilanes, see: (a) Matsumoto, T.; Kitano, Y.; Sato, F. Tetrahedron Lett. 1988, 29, 5685. (b) Kitano, Y.; Matsumoto, T.; Wakasa, T.; Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F.; Miyaji, K; Arai, K. Tetrahedron Lett. 1987, 28, 6351.
14. For alternative methods for preparing δ-hydroxy allylsilanes, see: (a) Matsumoto, T.; Kitano, Y.; Sato, F. Tetrahedron Lett. 1988, 29, 5685. (b) Kitano, Y.; Matsumoto, T.; Wakasa, T.; Okamoto, S.; Shimazaki, T.; Kobayashi, Y.; Sato, F.; Miyaji, K; Arai, K. Tetrahedron Lett. 1987, 28, 6351.
15. Tang, X. Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
16. For reviews of the utility of allylsilanes in other applications, see: (a) Roush, W. R. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.1, pp 1-53. (b) Fleming, I. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, pp 563-593. (c) Kleinman, E. F.; Volkman, R. A. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4.3, pp 975-1006.
17. For reviews of the utility of allylsilanes in other applications, see: (a) Roush, W. R. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.1, pp 1-53. (b) Fleming, I. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, pp 563-593. (c) Kleinman, E. F.; Volkman, R. A. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4.3, pp 975-1006.
18. For reviews of the utility of allylsilanes in other applications, see: (a) Roush, W. R. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.1, pp 1-53. (b) Fleming, I. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 2.2, pp 563-593. (c) Kleinman, E. F.; Volkman, R. A. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 4.3, pp 975-1006.
19. For related mechanistic proposals, see: (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (c) Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
20. For related mechanistic proposals, see: (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (c) Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
21. For related mechanistic proposals, see: (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (c) Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
22. For related mechanistic proposals, see: (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (c) Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
23. For related mechanistic proposals, see: (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (c) Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
24. For related mechanistic proposals, see: (a) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397. (c) Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579. (d) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (e) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (f) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
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