Novel [4 + 2] cycloaddition between thiobenzophenone and aryl-substituted alkenes via photoinduced electron transfer

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3587-3590

  Arguello, Juan E ^a   Pérez Ruiz, Raul ^b   Miranda, Miguel A ^b  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548542533     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7014384     Document Type: Article

References (36)

1. (a) Fringuelli, F.; Taticchi, A. The Diels - Alder Reaction; John Wiley & Sons: Chichester, U.K., 2002.
2. (b) Nicolaou, K. C.; Snyder, S. C.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
3. (c) Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779-4807.
4. (d) Robiette, R.; Marchand-Brynaert, J.; Peeters, D. J. Org. Chem. 2002, 67, 6823-6826.
5. (e) Berski, S.; Andrés, J.; Silvi, B.; Domingo, L. R. J. Phys. Chem. A 2006, 110, 13939-13947.
6. (a) Yueh, W.; Bauld, N. L. J. Phys. Org. Chem. 1996, 9, 529-538.
7. (b) Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124, 14147-14155.
8. (c) Saettel, N. J.; Wiest, O.; Singleton, D. A.; Meyer, M. P. J. Am. Chem. Soc 2002, 124, 11552-11559.
9. (d) Fukuzumi, S.; Okamoto, T.; Ohkubo, K. J. Phys. Chem. A 2003, 107, 5412-5418.
10. (e) Fürmeier, S.; Metzger, J. O. J. Am. Chem. Soc. 2004, 126, 14485-14492.
11. (f) Gomez-Bengoa, E.; Helm, M. D.; Plant, A.; Harrity, J. P. A. J. Am. Chem. Soc. 2007, 129, 2691-2699.
12. (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
13. (b) Tietze, L. F.; Kettschau, G. Hetero Diels-Alder reactions in organic chemistry. In Topics in Current Chemistry 189 (Stereoselective Heterocyclic Synthesis I); Metz, P., Ed.; Springer: Berlin, 1997; pp 1-120.
14. (a) Ohno, A.; Koizumi, T.; Ohnishi, Y. Bull. Chem. Soc. Jpn. 1971, 44, 2511-2515.
15. (b) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 13, 3471-3474.
16. (c) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417-1920.
17. (d) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147-4150.
18. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151-4155.
19. (f) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839-3845.
20. (g) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312-313.
21. (h) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339-1348.
22. (i) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445-1447.
23. (j) Beslin, P. J. Heterocycl. Chem. 1983, 20, 17531754.
24. (k) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131-1137.
25. (l) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122-1127.
26. (m) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943-2948.
27. (n) Liao, L.-F.; Tseng, P.-W.; Chou, C-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967-1977.
28. (o) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc, Perkin Trans. 1 1997, 2957-2959.
29. (p) Bachrach, S. M.; Jiang, S. J. Chem. Soc., Perkin Trans. 2 1998, 355-360.
30. (q) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001-1002.
31. (r) Li, G. M.; Niu, S.; Segi, M.; Tanaka, K.; Nakajima, T.; Zingaro, R. A.; Reibenspies, J. H.; Hall, M. B. J. Org. Chem. 2000, 65, 6601-6612.
32. Miranda, M. A.; Garcia, H. Chem. Rev. 1994, 94, 10631-1089.
33. (a) Breu, J.; Hoecht, P.; Rohr, U.; Schatz, J.; Sauer, J. Eur. J. Org. Chem. 1998, 2861-2873.
34. (b) Ohno, A.; Ohnishi, Y.; Tsuchihashi, G. J. Am. Chem. Soc. 1969, 91, 5038-5045.
35. Yueh, W.; Bauld, N. L. J. Phys. Org. Chem. 1996, 9, 529-538.
36. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271.