Umpolung of the reactivity of allylsilanes. Palladium(II) catalyzed cyclization of allylsilyl alcohols: A new route to substituted 2- vinyltetrahydrofurans

Tetrahedron Letters

Volumn 41, Issue 7, 2000, Pages 1119-1122

  MacSári, István ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZOQUINONE; COPPER CHLORIDE; DICHLOROMETHANE; METHANOL; PALLADIUM; PHOSPHORIC ACID; SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS;

EID: 0343384232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02245-5     Document Type: Article

References (21)

1. (a) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57.
2. (b) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
3. (c) Horn, K. A. Chem. Rev. 1995, 95, 1317.
4. (d) Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
5. (e) Wilson, S. R.; Augelli-Safran, C. E. Tetrahedron 1988, 44, 3983.
6. (f) Arimoto, M.; Yamaguchi, H.; Fujita, E.; Ochiai, M.; Nagao Y. Tetrahedron Lett. 1987, 28, 6298. Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Chem. Pharm. Bull. 1985, 33, 41 and 989.
7. (f) Arimoto, M.; Yamaguchi, H.; Fujita, E.; Ochiai, M.; Nagao Y. Tetrahedron Lett. 1987, 28, 6298. Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Chem. Pharm. Bull. 1985, 33, 41 and 989.
8. (g) Fuchigami, T.; Yamamoto, K. Chem. Lett. 1996, 937. Chiai, M.; Fujita, E., Arimoto, M.; Yamaguchi, H. Chem. Pharm. Bull. 1984, 32, 5027.
9. (g) Fuchigami, T.; Yamamoto, K. Chem. Lett. 1996, 937. Chiai, M.; Fujita, E., Arimoto, M.; Yamaguchi, H. Chem. Pharm. Bull. 1984, 32, 5027.
10. (h) Hu, N. X.; Aso, Y.; Otsubo, T.; Ogura, F. Tetrahedron Lett. 1998, 29, 4949.
11. (i) Yoshida, J.; Murata, T.; Isoe, S. Tetrahedron Lett. 1986, 27, 3373. Takanami, T.; Suda, K.; Ohomori, H.; Masui, M. Chem. Lett. 1986, 1335.
12. (i) Yoshida, J.; Murata, T.; Isoe, S. Tetrahedron Lett. 1986, 27, 3373. Takanami, T.; Suda, K.; Ohomori, H.; Masui, M. Chem. Lett. 1986, 1335.
13. (j) Riahi, A.; Cossy, J.; Muzart, J.; Pete, J. P. Tetrahedron Lett. 1985, 26, 839.
14. (a) Macsári, I.; Hupe, E.; Szabó, K. J. J. Org. Chem. 1999, 64, 9547.
15. (b) Bäckvall, J.-E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
16. (c) Hansson, S.; Heumann, A.; Rein, T.; Åkermark, B. J. Org. Chem. 1990, 55, 975.
17. 4. Removal of the solvent in vacuo and purification of the residual oil by chromatography in pentane/ether afforded the corresponding product.
18. (a) Kliegman, J. M. J. Organomet. Chem. 1971, 29, 73.
19. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1983, 736.
20. (c) Ogoshi, S.; Yoshida, W.; Ohe, K.; Murai, S. Organometallics 1993, 12, 578.
21. Szabó, K. J. Organometallics 1998, 17, 1677.