Stereo- and regioselective zinc-mediated ring-opening of epoxides with diselenides

Synlett

Volumn , Issue 8, 2005, Pages 1316-1318

  Movassagh, Barahman ^a   Shamsipoor, Mojgan ^a  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

hydroxy selenides; Diselenides; Epoxides; Zinc; Zinc selenolate

Indexed keywords

ACETONITRILE; ALUMINUM CHLORIDE; BETA HYDROXYSELENIDE; DISELENIDE; EPOXIDE; SELENIDE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG; ZINC;

AQUEOUS SOLUTION; ARTICLE; INTERMETHOD COMPARISON; ISOMER; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 19944373067     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865224     Document Type: Article

References (34)

1. Krief, A. Tetrahedron 1980, 36, 2531.
2. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697.
3. Reich, H. J.; Chow, F. J. Chem. Soc., Chem. Commun. 1975, 1135.
4. (a) Sevring, M.; Dumount, W.; Henesi, L.; Krief, A. Tetrahedron Lett. 1976, 2647.
5. (b) Holzle, G.; Jenny, W. Helv. Chim. Acta 1958, 41, 712.
6. (a) Van Ende, D.; Dumount, W.; Krief, A. Angew. Chem., Int. Ed. Engl. 1975, 14, 700.
7. (b) Van Ende, D.; Krief, A. Tetrahedron Lett. 1976, 457.
8. (c) Dumount, W.; Krief, A. Angew. Chem., Int. Ed. Engl. 1975, 14, 350.
9. Labar, D.; Krief, A.; Hevesi, L. Tetrahedron Lett. 1978, 3967.
10. Denis, J. N.; Vicens, J.; Krief, A. Tetrahedron Lett. 1979, 2697.
11. (a) Clive, D. L. J. Tetrahedron 1978, 34, 1049.
12. (b) Sharpless, K. B.; Lauer, R. F. J. Org. Chem. 1974, 39, 429.
13. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704.
14. (a) Labar, D.; Laboureur, J. L.; Krief, A. Tetrahedron Lett. 1982, 23, 983.
15. (b) Laboureur, J. L.; Krief, A. Tetrahedron Lett. 1984, 25, 2713.
16. (c) Labar, D.; Krief, A. J. Chem. Soc., Chem. Commun. 1983, 564.
17. Leonard-Coppens, A. M.; Krief, A. Tetrahedron Lett. 1976, 3227.
18. Halazy, S.; Krief, A. Tetrahedron Lett. 1981, 22, 1833.
19. Detty, M. R. Tetrahedron Lett. 1978, 5087.
20. (a) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821.
21. (b) Bartlett, P. A.; McQuaid, L. A. J. Am. Chem. Soc. 1984, 106, 7854.
22. Cravador, A.; Krief, A. Tetrahedron Lett. 1981, 22, 2491.
23. Posner, G. H.; Rogers, D. Z. J. Am. Chem. Soc. 1977, 99, 8208.
24. (a) Movassagh, B.; Shamsipoor, M. Synlett 2005, 121.
25. (b) Movassagh, B.; Shamsipoor, M.; Joshaghani, M. J. Chem. Res., Synop. 2004, 148.
26. (c) Movassagh, B.; Mirshojaei, F. Monatsh. Chem. 2003, 134, 831.
27. 2O = 2:1) to afford the desired β-hydroxy selenides.
28. 4), and evaporated. Preparative TLC yielded the pure products.
29. Sakakibara, M.; Katsumata, K.; Watanabe, Y.; Toru, T.; Ueno, Y. Synthesis 1992, 377.
30. Nishiyama, Y.; Ohashi, H.; Itoh, K.; Sonoda, N. Chem. Lett. 1998, 159.
31. Wang, L.; Zhang, Y. J. Chem. Res., Synop. 1998, 598.
32. Devan, N.; Sridhar, P. R.; Prabhu, K. R.; Chandrasekaran, S. J. Org. Chem, 2002, 67, 9417.
33. Wang, J. X.; Xi, Y.; Du, Z.; Zhao, K. Synth. Commun. 2000, 30, 2661.
34. Toshimitsu, A.; Aoai, T.; Owada, H.; Uemura, S.; Okano, M. Tetrahedron 1985, 41, 5301.