Synthesis of enantiomerically pure substituted tetrahydrofurans from epoxides and phenylselenium reagents

Tetrahedron Asymmetry

Volumn 15, Issue 3, 2004, Pages 405-412

  Tiecco, Marcello ^a   Testaferri, Lorenzo ^a   Bagnoli, Luana ^a   Purgatorio, Valentina ^a   Temperini, Andrea ^a   Marini, Francesca ^a   Santi, Claudio ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ANION; EPOXIDE; FURAN DERIVATIVE; REAGENT; SELENIDE; SELENIUM; SELENIUM DERIVATIVE;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; PRIORITY JOURNAL; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EID: 0742306898     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.042     Document Type: Article

References (25)

1. Tiecco M. Wirth T. Electrophilic Selenium, Selenocyclizations. Topics in Current Chemistry: Organoselenium Chemistry: Modern Developments in Organic Synthesis. 2000;7-54 Springer, Heidelberg.
2. Back T.G. Organoselenium Chemistry - A Pratical Approach. 2000;Oxford, New York.
3. Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis. 1986;Pergamon, Oxford.
4. Fragale G., Wirth T. Eur. J. Org. Chem. 1998;1361-1369.
5. Deziel R., Malenfant E. J. Org. Chem. 60:1995;4660-4662.
6. Nishibayashi Y., Srivastava S.K., Takada H., Fukuzawa S., Uemura S. J. Chem. Soc., Chem. Commun. 1995;2321-2322.
7. Back T.G., Dyck B.P., Nan S. Tetrahedron. 55:1999;3191-3208.
8. Takada H., Nishibayashi Y., Uemura S. J. Chem. Soc., Perkin Trans. 1. 1999;1511-1516.
9. Fujita K., Murata K., Iwaoka M., Tomoda S. J. Chem. Soc., Chem. Commun. 1995;1641-1642.
10. Fujita K., Murata K., Iwaoka M., Tomoda S. Tetrahedron. 53:1997;2029-2048.
11. Deziel R., Malenfant E., Thibault C., Frechette S., Gravel M. Tetrahedron Lett. 38:1997;4753-4756.
12. Wirth T. Tetrahedron. 55:1999;1-28.
13. Wirth T. Angew. Chem., Int. Ed. 39:2000;3740-3749.
14. Tiecco M., Testaferri L., Bagnoli L., Marini F., Temperini A., Tomassini C., Santi C. Tetrahedron Lett. 41:2000;3241-3245.
15. Tiecco M., Testaferri L., Santi C., Tomassini C., Marini F., Bagnoli L., Temperini A. Chem. Eur. J. 8:2002;1118-1124.
16. Tiecco M., Testaferri L., Marini F., Sternativo S., Bagnoli L., Santi C., Temperini A. Tetrahedron: Asymmetry. 12:2001;1493-1502.
17. Tiecco M., Testaferri L., Bagnoli L., Purgatorio V., Temperini A., Marini F., Santi C. Tetrahedron: Asymmetry. 12:2001;3297-3304.
18. Angle S.R., White S.L. Tetrahedron Lett. 41:2000;8059-8062. and references cited therein.
19. Harmange J.-C., Figadere B. Tetrahedron: Asymmetry. 4:1993;1711-1754.
20. Miura K., Okajima S., Hondo T., Nakagawa T., Takahashi T., Hosomi A. J. Am. Chem. Soc. 122:2000;11348-11357. and references cited therein.
21. Olivier A., Laurent D., Landais Y., Planchenault D., Weber V. Tetrahedron. 53:1997;4339-4352.
22. Von dem Bussche-Hunnefeld J.L., Seebach D. Tetrahedron. 48:1992;5719-5730.
23. Tiecco M., Testaferri L., Santi C., Tomassini C., Marini F., Bagnoli L., Temperini A. Tetrahedron: Asymmetry. 13:2002;429-435.
24. Bernardi L., Bonini B.M., Comes-Franchini M., Fochi M., Mazzanti G., Ricci A., Varchi G. Eur. J. Org. Chem. 2002;2776-2784.
25. Abenhaim D., Namy J.L., Boireau G. Bull. Soc. Chim. Fr. 9:1971;3254-3258.