Sequential Diels-Alder and cobalt octacarbonyl catalyzed Pauson-Khand reactions in the formation of polycyclic enones

Synlett

Volumn , Issue 12, 2007, Pages 1857-1862

  Soo, Young Choi ^a   Sang, Ick Lee ^a   Kang, Hyun Park ^a   Young, Keun Chung ^a  

^a Seoul National University   (South Korea)

Author keywords

Cobalt; Diels Alder; Dienynes; Pauson Khand; Tandem

Indexed keywords

CARBONYL DERIVATIVE; COBALT OCTACARBONYL; DIENOPHILE DERIVATIVE; DIENYNE DERIVATIVE; ENONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ONE POT SYNTHESIS; PAUSON KHAND REACTION; X RAY CRYSTALLOGRAPHY;

EID: 34547661989     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984511     Document Type: Article

References (34)

1. For recent leading papers, see: (a) Sun, J. W.; Conley, M. P.; Zhang, L. M.; Kozmin, S. A. J. Am. Chem. Soc. 2006, 128, 9705.
2. (b) Jimenes-Nunez, E.; Claverie, C. K.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2006, 45, 5452.
3. (c) Evans, P. A.; Sawyer, J. R.; Lai, K. W.; Hufman, J. C. Chem. Commun. 2005, 3971.
4. (d) Chen, Y. H.; Douglas, M.; Lee, C. J. Am. Chem. Soc. 2005, 127, 12184.
5. (e) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
6. (f) Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 7875.
7. (a) Maifeld, S. V.; Lee, D. Chem. Eur. J. 2005, 11, 6118.
8. (b) Gonzalez-Gomez, M.; Dominguez, G.; Castells, J. P. Tetrahedron Lett. 2005, 46, 7267.
9. (c) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047.
10. (d) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323.
11. (e) Efskind, J.; Undheim, K. Tetrahedron Lett. 2003, 44, 2837.
12. (f) Smulik, J. A.; Diver, S. T. Tetrahedron Lett. 2001, 42, 171.
13. (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432.
14. (b) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843.
15. (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255.
16. (d) Paik, S.-J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045.
17. (e) Wang, B.; Cao, P.; Zhang, X. M. Tetrahedron Lett. 2000, 41, 8041.
18. (f) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077.
19. (g) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047.
20. (h) Murakami, M.; Ubukata, M.; Kami, K.; Ito, Y. Angew. Chem. Int. Ed. 1998, 37, 2248.
21. (i) Heath, H.; Wolfe, B.; Livinghouse, T.; Bae, S. K. Synthesis 2001, 2341.
22. (a) Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem. Int. Ed. 2003, 42, 1853.
23. (b) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem. Int. Ed. 2004, 43, 3076.
24. Park, K. H.; Choi, S. Y.; Chung, Y. K. Synlett 2006, 527.
25. For recent reviews, see: (a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
26. (b) Fogg, D. E.; dos Santos, E. N. Coord. Chem. Rev. 2004, 248, 2365.
27. (c) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302.
28. (d) Ajamian, A.; Gleason, J. L. Angew. Chem. Int. Ed. 2004, 43, 3754.
29. Kim, D. H.; Chung, Y. K. Chem. Commun. 2005, 1634.
30. (a) Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73.
31. (b) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc 2000, 122, 6771.
32. (c) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
33. Yeh, M.-C.; Tsao, W.-C.; Ho, J.-S.; Tai, C.-C.; Chiou, D.-Y.; Tu, L.-H. Organometallics 2004, 23, 792.
34. 3): δ = 16.5, 30.5, 40.2, 41.4, 42.9,...