Diels-Alder reaction between indoles and cyclohexadienes photocatalyzed by a (thia)pyrylium salt

Arkivoc

Volumn 2007, Issue 4, 2007, Pages 344-355

  González Béjar, María ^a   Stiriba, Salah Eddine ^a   Miranda, Miguel A ^b   Pérez Prieto, Julia ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

1,3 cyclohexadienes; Diels Alder reaction; Indoles; Photocatalysis; Thiapyrylium salts

Indexed keywords

EID: 33846081001     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.431     Document Type: Article

References (24)

1. 60 and Danishefsky's dienes: Mikami, K.; Matsumoto, S.; Okubo, Y.; Fujitsuka, M.; Ito, O.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 2000, 122, 2236.
2. (b) Strained dienophiles can also lead to [4+2] adducts: Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2002, 4, 11.
3. Some thermal Diels-Alder reactions between electron-rich components are metal-catalyzed processes: Hilt, G.; Smolko, K. I. Synthesis 2002, 686.
4. (a) Mattay, J.; Trampe, G.; Runsink, J. Chem. Ber. 1988, 121, 1991.
5. (b) Mattay, J.; Vondenhof, M.; Denig, R. Chem. Ber. 1989, 122, 951.
6. (a) Pabon, R. A.; Bellvile, D. J.; Bauld, N. L. J. Am. Chem. Soc. 1983, 105, 5158.
7. (b) Schmittel, M.; von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165.
8. (c) Bauld, N. L.; Yang, J.; Gao, D. J. Chem.Soc., Perkin Trans. 2 2000, 207.
9. (a) Calhoun, G. C.; Schuster, G. B. Tetrahedron Lett. 1986, 27, 911.
10. (b) Akbulut, N.; Hartsough, D.; Kim, J. I.; Schuster, G. B. J. Org. Chem. 1989, 54, 2549.
11. (c) Kim, J. I.; Schuster, G. B. J. Am. Chem. Soc. 1992, 114, 9309.
12. (a) Gieseler, A.; Steckhan, E.; Wiest, O.; Knoch, F. J. Org. Chem. 1991, 56, 1405.
13. (b) Wiest, O.; Steckhan, E. Tetrahedron Lett. 1993, 34, 6391.
14. (a) Pérez-Prieto, J.; Stiriba, S.-E.; González- Béjar, M.; Domingo, L. R.; Miranda, M. A. Org. Lett. 2004, 6, 3905.
15. (b) González-Béjar, M.; Stiriba, S.-E.; Domingo, L. R.; Pérez-Prieto, J.; Miranda, M. A. J. Org. Chem. 2006, 71, 6932.
16. Martiny, M.; Steckhan, E.; Esch, T. Chem. Ber. 1993, 126, 1671.
17. Saeva, F. D.; Olin, G. R. J. Am. Chem. Soc. 1980, 102, 299.
18. Jayanthi, S. S.; Ramamurthy, P. J. Phys. Chem. A 1998, 102, 511.
19. +], 173 (53), 131 (100).
20. Miranda, M. A.; Izquierdo, M. A.; Pérez-Ruiz, R. J. Phys. Chem. A 2003, 107, 2478.
21. Pérez-Prieto, J.; Bosca, F.; Galian, R. E.; Lahoz, A.; Domingo, L. R.; Miranda, M. A. J. Org. Chem. 2003, 68, 5104.
22. Miranda, M. A.; García, H. Chem. Rev. 1994, 94, 1063.
23. Akaba, R.; Kamata, M.; Koike, A.; Mogi, K-I.; Kuriyama, Y.; Sakuragi, H. J. Phys. Org. Chem. A 1997, 10, 861.
24. Julliard, M.; Chanon, M. Chem. Rev. 1983, 83, 425.