Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10204-10205

  Zhang, Liming ^a   Kozmin, Sergey A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; ACID; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BRONSTED ACID; KETENE DERIVATIVE; LEWIS ACID; POLYCYCLIC AROMATIC HYDROCARBON; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLIZATION; ELECTRON; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS;

EID: 4143058102     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046586x     Document Type: Article

References (30)

1. For representative examples, see: (a) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339.
2. (b) Fernandes-Rivas, C.; Mendez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221.
3. (c) Chatani, N.; Inoue, H.; Ikeda, T.; Murai, S. J. Org. Chem. 2000, 65, 4913.
4. (d) Asao, N.; Shimada, T.; Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 10899.
5. (e) Inoue, H.; Chatani, N.; Murai, S. J. Org. Chem. 2002, 67, 1414.
6. (f) Fürstner, A.; Mamune, V. J. Org. Chem. 2002, 67, 6264.
7. (g) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
8. (h) Nishizawa, M.; Takao, H.; Yadav, V. K.; Imagawa, H.; Sugihara, T. Org. Lett. 2003, 5, 4563.
9. For representative Brønsted acid-mediated enyne cyclizations, see: (a) Johnson, W. S.; Gravestock, M. B.; Parry, R. J.; Myers, R. F.; Bryson, T. A.; Miles, D. H. J. Am. Chem. Soc. 1971, 93, 4330.
10. (b) Fürtsner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
11. For our studies on the reactivity of siloxyalkynes, see: (a) Schramm, M. P.; Reddy, D. S.; Kozmin, S. A. Angew. Chem., Int. Ed. 2001, 40, 4274.
12. (b) Sweis, R. F.; Schramm, M. P.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 7442.
13. (c) Reddy, D. S.; Kozmin, S. A. J. Org. Chem. 2004, 69, 4860.
14. For a recent review of ynolates, see: Shindo, M. Synthesis. 2003, 2275.
15. (a) Staudinger, H. Die Ketene; Verlag Enke: Stuttgart, 1912.
16. (b) Tidwell, T. T. Ketenes; John Wiley & Sons, Inc.: New York, 1995.
17. (c) Chemistry of Ketenes, Allenes and Related Compounds; Patar, S., Ed.; John Wiley & Sons: New York, 1980.
18. (a) Hegmann, J.; Ditterich, E.; Hüttner, G.; Christl, M.; Peters, E.; Peters, K.; Vor Schnering, H. G. Chem. Ber. 1992, 125, 1913.
19. (b) Uhlig, W.; Tzschach, A. Z. Chem. 1988, 28, 409. Also see ref 4b.
20. For β-functionalization of alkoxy alkynes to give ketenes, see: (a) Ponomarev, S. C. Angew. Chem. Int. Ed. Engl. 1973, 12, 675.
21. (b) Danishefsky, S.; Kitahara, T.; Tsai, M.; Dynak, J. J. Org. Chem. 1976, 41, 1669.
22. (c) Sakurai, H.; Shirahata, A.; Sasaki, K.; Hosomi, A. Synthesis 1979, 740.
23. (d) Himbert, G.; Henn, L. Tetrahedron Lett. 1984, 25, 1357.
24. Siloxyalkynes utilized in this study were prepared by the following method: Julia, M. Saint-Jalmes, V. P.; Verpeaux, J. N. Synlett 1993, 233.
25. 2-promoted reactions, see: (a) Foropoulus, J.; DesMarteau, D. D. Inorg. Chem. 1984, 23, 3720.
26. (b) Kuhnert, N.; Peverley, J.; Roberston, J. Tetrahedron Lett. 1998, 39, 3215.
27. (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851.
28. (d) Cossy, J.; Lutz, F.; Alauze, V.; Meyer, C. Synlett 2002, 45.
29. 2, see: Thomazeau, C.; Bourbigou, H. O.; Magna, L.; Luts, S.; Gilbert, B. J. Am. Chem. Soc. 2003, 125, 5264 and references therein.
30. For complete details, see Supporting Information.