A new cycloisomerization reaction: Formation of eight-membered-ring compounds from 3-sila 1,7-enynes

Organometallics

Volumn 15, Issue 26, 1996, Pages 5439-5441

  Kagoshima, Hirotaka ^a   Hayashi, Minoru ^a   Hashimoto, Yukihiko ^a   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3643074061     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9606294     Document Type: Article

References (32)

1. For recent reviews on the Pauson-Khand reaction, see: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 1037. (c) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 703.
2. For recent reviews on the Pauson-Khand reaction, see: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 1037. (c) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 703.
3. For recent reviews on the Pauson-Khand reaction, see: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 1037. (c) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 703.
4. (a) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289.
5. (b) Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S.-E. Synlett 1991, 204.
6. (c) Krafft, M. E.; Romero, R. H.; Scott, I. L. J. Org. Chem. 1992, 57, 5277.
7. (d) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
8. (e) Jeong, N.; Lee, B. Y.; Lee, S. M.; Chung, Y. K.; Lee, S.-G. Tetrahedron Lett. 1993, 34, 4023.
9. (f) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
10. Smit, W. A.; Buhanjuk, S. M.; Simonyan, S. O.; Shashkov, A. S.; Struchkov, Y. T.; Yanovsky, A. I.; Caple, R.; Gybin, A. S.; Anderson, L. G.; Whiteford, J. A. Tetrahedron Lett. 1991, 32, 2105 and references therein.
11. In the reaction of alkynes with electron-deficient alkenes under the Pauson-Khand conditions, the corresponding dienyl products have been obtained: Khand, I. U.; Pauson, P. L. J. Chem. Soc., Chem. Commun. 1974, 379.
12. For a recent review, see: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
13. (a) Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268.
14. (b) Trost, B. M.; Gelling, O. J. Tetrahedron Lett. 1993, 34, 8233.
15. (c) Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255.
16. (d) Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
17. Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211.
18. (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737.
19. (b) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
20. (c) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
21. (d) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901.
22. Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
23. 2O (0.68 g, 5.0 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 1 h. A purple precipitate formed. The resulting mixture was concentrated and filtered through a short silica gel plug (eluent: 5/1 hexane/ethyl acetate), and the eluent was concentrated. Purification of the crude product by PTLC (eluent: 30/1 hexane/ethyl acetate) gave 2 (63 mg, 46%).
24. (a) Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
25. (b) Brown, S. W.; Pauson, P. L. J. Chem. Soc., Perkin Trans. 1 1990, 1205.
26. (c) Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388.
27. (d) Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E. Tetrahedron: Asym. 1994, 5, 307.
28. 3) δ 2.52 (dt, 2H, J = 5.6, 8.6 Hz), 3.91 (t, 2H, J = 5.6 Hz), 5.73 (dt, 1H, J = 8.6, 11.5 Hz), 5.98 (d, 1H, J = 14.8 Hz), 6.31 (dd, 1H, J = 4.4, 11.5 Hz), 6.84 (dd, 1H, J = 4.4, 14.8 Hz), 7.32-7.63 (m, 10H).
29. X-ray crystal data for 4: Triclinic; P1; colorless crystal; a = 9.415(1), b = 11.909(2), c = 7.697(1) Å; α = 96.56(1), β = 113.02(1), γ = 89.57(1)°; Z = 2; R = 0.043; GOF = 0.30. For full details, see the Supporting Information.
30. The Pd-catalyzed cycloisomerization reaction of 1,6-enynes to cycloheptadiene derivatives has been reported: Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647.
31. (a) Colvin, E. W. Silicon in Organic Synthesis; Butterworths: London, 1981; pp 10, 21.
32. (b) Takeuchi, R.; Ishii, N.; Sugiura, M.; Sato, N. J. Org. Chem. 1992, 57, 4189.