Highly stereoselective 6π electrocyclization of bridged bicyclic 1,3,5-trienes

Organic Letters

Volumn 9, Issue 13, 2007, Pages 2545-2548

  Benson, Chantel L ^a   West, F G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547145210     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070924s     Document Type: Article

References (36)

1. (a) Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757-4778.
2. (b) Tantillo, D. J. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2006, 102, 269-289.
3. (a) Mazzola, R. D., Jr.; White, T. D.; Vollmer-Snarr, H. R.; West, F. G. Org. Lett. 2005, 7, 2799-2801.
4. (b) White, T. D.; West, F. G. Tetrahedron Lett. 2005, 46, 5629-5632.
5. (c) Giese, S.; Mazzola, R. D., Jr.; Amann, C. M.; Arif, A. M.; West, F. G. Angew. Chem., Int. Ed. 2005, 44, 6546-6549.
6. Recent reviews of the Nazarov reaction: (a) Pellisier, H. Tetrahedron 2005, 61, 6479-6517.
7. (b) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577-7606.
8. (c) Review: Tius, M. A. Eur. J. Org. Chem. 2005, 2193-2206.
9. Magomedov, N. A.; Ruggiero, P. L.; Tang, Y. Org. Lett. 2004, 6, 3373-3375.
10. Tessier, P. E.; Nguyen, N.; Clay, M. D.; Fallis, A. G. Org. Lett. 2005, 7, 767-770.
11. For a review of Pd-catalyzed alkynylation chemistry, see: Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2018.
12. Mazzola, R. D., Jr.; Giese, S.; Benson, C. L.; West, F. G. J. Org. Chem. 2004, 69, 220-223.
13. (a) 3a: Michel, P.; Gennet, D.; Rassat, A. Tetrahedron Lett. 1999, 40, 8575-8578.
14. (b) 3b: Fiandanese, V.; Marchese, G.; Punzi, A.; Ruggieri, G. Tetrahedron Lett. 1996, 37, 8455-8458.
15. (c) 3c: Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815-3818.
16. Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5560-5562.
17. Hayashi, R.; Fernandez, S.; Okamura, W. H. Org. Lett. 2002, 4, 851-854.
18. Oves, D.; Ferrero, M.; Fernandez, S.; Gotor. V. J. Org. Chem. 2003, 68, 1154-1157.
19. (a) Marvell, E. N.; Tashiro, J. J. Org. Chem. 1965, 30, 3991-3993.
20. (b) Paquette, L. A.; Chang, J.; Liu, Z. J. Org. Chem. 2004, 69, 6441-6448.
21. (c) Kumar, P.; Naidu, S. V.; Gupta, P. J. Org. Chem. 2005, 70, 2843-2846.
22. (a) Nicolaou, K. C.; Ladduwahetty, T.; Taffer, I. M.; Zipkin, R. E. Synthesis 1986, 344-347.
23. (b) Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1998, 110, 2248-2256.
24. Boland, W.; Schroer, N.; Sieler, C.; Feigel, M. Helv. Chim. Acta 1987, 70, 1025-1040.
25. (a) Alami, M.; Crousse, B.; Linstrumelle, G. Tetrahedron Lett. 1994, 35, 3543-3544.
26. (b) Borhan, B.; Souto, M. L.; Um, J. M.; Zhou, B.; Nakanishi, K. Chem. Eur. J. 1999, 5, 1172-1175.
27. (c) Nesnas, N.; Rando, R. R.; Nakanishi, K. Tetrahedron 2002, 58, 6577-6584.
28. 1H NMR chemical shift trends. See the Supporting Information for a discussion.
29. (a) Schleyer, P. v. R. J. Am. Chem. Soc. 1967, 89, 701-703.
30. (b) Brown, H. C.; Kawakami, J. H.; Liu, K.-T. J. Am. Chem. Soc. 1973, 95, 2209-2216.
31. (c) Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4054-4061.
32. (d) Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2436-2438.
33. (e) Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974-4976.
34. 3.
35. (a) Suffert, J.; Salem, B.; Klotz, P. J. Am. Chem. Soc. 2001, 123, 12107-12108.
36. (b) von Essen, R.; Frank, D.; Sünnemann, H. W.; Vidovic, D.; Mugull, J.; de Meijere, A. Chem. Eur. J. 2005, 11, 6583-6592.