6πe- versus 8πe- electrocyclization of 1-aryl-And heteroaryl-substituted

Organic Letters

Volumn 11, Issue 4, 2009, Pages 983-986

  García Rubín, Silvia ^a   Varela, Jesús A ^a   Castedo, Luis ^a   Saa, Carlos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 64349124950     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802925q     Document Type: Article

References (36)

1. (1Z, 3Z) -1, 3, 5-Hexatrienes: A Matter of Aromaticity
2. (1) (a) Fukui, K. Acc. Chem. Res. 1971, 4, 57.
3. (b) Woodward, R. B.; Hoffmann, R. The ConserVation of Orbital Symmetry; Verlag Chemie International: Deerfield Beach, FL, 1970.
4. (2) (a) Pindur, U.; Schneider, G. H. Chem. Soc. Rev. 1994, 409.
5. (b) Trost, B. M.; Fleming, I.; Paquette, L. A. ComprehensiVe Organic Synthesis; Pergamon: Oxford, U. K., 1991; Vol. 5, pp 675-784.
6. (c) Marvell, E. N. Thermal Electrocyclic Reactions; Academic Press: New York, 1980.
7. (3) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395. (4) (3Z) -1, 3, 5-Hexatrienes and (3Z, 5Z) -1, 3, 5, 7-octatetraenes can be efficiently prepared by Ru-catalyzed linear coupling of 1, 6-diynes to alkenes and 1, 3-dienes, respectively. (a) García- Rubín, S.; Varela, J. A.; Castedo, L.; Saá, C. Chem. Eur. J. 2008, 14, 9772.
8. (b) Varela, J. A.; Rubín, S. G.; González-Rodríguez, C.; Castedo, L.; Saá, C. J. Am. Chem. Soc. 2006, 128, 9262.
9. (c) Varela, J. A.; Castedo, L.; Saá, C. Org. Lett. 2003, 5, 2841.
10. (5) Lecea, B.; Arrieta, A.; Cossio, F. P. J. Org. Chem. 2005, 70, 1035.
11. (6) 1, 3, 5-Hexatrienylarenes 3 were obtained by Ru-catalyzed linear coupling of diynes 1 and (Z) -1, 3-dienes 2, while (E) -1, 3-dienes 2 failed to give the linear coupling reaction. See ref 4 for more details and Supporting Information for X-ray data for compound 3a.
12. (7) For reviews on met al.-mediated cyclooctanoid construction, see: (a) Yet, L. Chem. Rev. 2000, 100, 2963.
13. (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881. For [2 + 2 + 2 + 2] cycloadditions, see:
14. (c) Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2007, 129, 13402.
15. (d) Bouissie, T. R.; Streitwieser, A. J. Ore. Chem. 1993, 58, 2377.
16. (e) Walther, D.; Braun, D.; Schulz, W.; Rosenthal, U. Z. Anorg. Allg. Chem. 1998, 577, 270.
17. (f) Diercks, R.; Stamp, L.; tom Dieck, H. Chem. Ber. 1984, 117, 1913. For [4 + 2 + 2] cycloadditions, see:
18. (g) DeBoef, B.; Counts, W. R.; Gilbertson, S. R. J. Org. Chem. 2007, 72, 799.
19. (h) Wender, P. A.; Christy, J. P. J. Am. Chem Soc. 2006, 128, 5354.
20. (i) Murakami, M.; Ashida, S.; Matsuda, T. J. Am. Chem. Soc. 2006, 128, 2166.
21. (j) Baik, M. H.; Baum, E. W.; Burland, M. C.; Evans, P. A. J. Am. Chem. Soc. 2005, 127, 1602. For [5 + 2+1] cycloadditions, see:
22. (k) Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z. X., J. Am. Chem. Soc. 2007, 129, 10060. For [4 + 4] cycloadditions, see:
23. (l) Murakami, M.; Itami, K.; Ito, Y. Synlett., 1999, 951.
24. (m) Sieburth, S. M.; Cunard, N. T. Tetrahedron 1996, 52, 6251.
25. (n) Baldenius, K.-U.; tom Dieck, H.; Koning, W. A.; Icheln, D.; Runge, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 305.
26. (o) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. For [6 + 2] cycloadditions, see:
27. (p) Tenaglia, A.; Gaillard, S. Angew. Chem., Int. Ed. 2008, 47, 2454.
28. (q) Wender, P. A.; Correa, A. G.; Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122, 7815.
29. (r) Achard, M.; Mosrin, M.; Tenaglia, A.; Buono, G. J. Org. Chem. 2006, 71, 2907.
30. - electrocyclic reactions, see ref 5. For other examples of cascade met al.-mediated reactions /electrocyclization, see:
31. (c) Kan, S. B. J.; Anderson, E. A. Org. Lett. 2008, 10, 2323.
32. (d) Salem, B.; Suffert, J. Angew. Chem. Int. Ed. 2004, 43, 2826.
33. (e) von Zezschwitz, P.; Petry, F.; de Meijere, A. Chem. Eur. J. 2001, 7, 4035.
34. (f) de Meijere, A.; Brase, S. J. Organomet. Chem. 1999, 576, 88.
35. (9) The isomeric 9- (propenyl) anthracene did not participate in the reaction, probably due to steric hindrance caused by the anthracene ring.
36. (10) See Supporting Information for X-ray data for compounds 10c and 9f.