Highly efficient gold-catalyzed atom-economical annulation of phenols with dienes

Organic Letters

Volumn 8, Issue 11, 2006, Pages 2397-2399

  Nguyen, Rene Viet ^a   Yao, Xiaoquan ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745697752     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0607692     Document Type: Article

References (32)

1. For selected reviews on gold catalysis, see: (a) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2005, 43, 6990.
2. (b) Hashmi, A. S. K. Gold Bull 2004, 37, 3.
3. (c) Dyker, G. Angew. Chem., Int. Ed. 2000, 39, 4237.
4. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
5. Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
6. Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
7. (a) Liu, Y.; Song, F.; Song, Z.; Liu. M.; Yan, B. Org. Lett. 2005, 7, 5409.
8. (b) Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3925.
9. Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964.
10. (a) Antoniotti, S.; Genin, E.; Michelet, V.; Genêt, J.-P. J. Am. Chem. Soc. 2005, 127, 9976.
11. (b) Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804.
12. For a recent review on the cycloisomerization of enynes, see: Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200.
13. Sato, K.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2005, 70, 8977.
14. (a) Wei, C. M.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
15. (b) Gold-catalyzed addition of alkyne to aldehyde was also developed recently, see: Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
16. Luo, Y.; Li, C.-J. Chem. Commun. 2004, 1930.
17. Georgy, M.; Boucard, V.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 14180.
18. Yang, C.-G.; He, C. J. Am. Chem. Soc. 2005, 127, 6966.
19. (a) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669.
20. (b) Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485.
21. Yao, X.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 6884.
22. Nguyen, R.-V.; Yao, X.; Bohle, D. S.; Li, C.-J. Org. Lett. 2005, 7, 673.
23. For similar reactions by other catalysts, see: (a) Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002.
24. (b) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648.
25. (c) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, /26, 4526.
26. (d) Leitner, A.; Larsen, J.; Steffens, C.; Hartwig, J. F. J. Org. Chem. 2004, 69, 7552.
27. Bioactive Compounds from Natural Sources; Tringali, C., Ed.; Taylor & Francis: New York, 2001.
28. (a) Trost, B. M. Science 1991, 254, 1471.
29. (b) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
30. Nguyen, R.-V.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 17184.
31. For a recent gold-catalyzed hydroamination of alkene, see: Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
32. Gold-catalyzed hydroamination of diene: Brouwer, C.: He, C. Angew. Chem., Int. Ed. 2006, 45, 1744.