A chiral electrophilic selenium reagent to promote the kinetic resolution of racemic allylic alcohols

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4751-4753

  Tiecco, Marcello ^a   Testaferri, Lorenzo ^a   Santi, Claudio ^a   Tomassini, Cristina ^a   Bonini, Rosaria ^a   Marini, Francesca ^a   Bagnoli, Luana ^a   Temperini, Andrea ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; METHANOL; REAGENT; SELENIUM;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHIRALITY; KINETICS; RACEMIC MIXTURE;

EID: 11444259969     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048001+     Document Type: Article

References (25)

1. (a) Adam, W.; Alsters, P. L.; Neuman, R.; Saha-Moeller, C. R.; Sloboda-Rozner, D.; Zhang, R. J. Org. Chem. 2003, 68, 1721.
2. (b) Adam, W.; Alsters, P. L.; Neuman, R.; Saha-Moeller, C. R.; Sloboda-Rozner, D.; Zhang, R. Synlett 2002, 2011.
3. (c) Adam, W.; Botke, N. J. Am. Chem. Soc. 2000, 122, 9846.
4. (d) Charlette, A.; Lebel, H.; Gagnon, A. Tetrahedron 1999, 55, 8845.
5. (a) Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
6. (b) Gau, A.; Lin, G.; Uang, B.; Liao, F.; Wang, S. J. Org. Chem. 1999, 64, 2194.
7. Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703.
8. (a) Ohkuma, T.; Ikehira, H.; Ihariya, T.; Noyori, R. Synlett 1997, 467.
9. (b) Yadav, J.; Reddy, B.; Reddy, K. Tetrahedron 2003, 59, 5333.
10. Schneider, C.; Kazmaier, U. Synthesis 1998, 1314.
11. Kamal, A.; Sandbhor, M.; Shaik, A.; Sravanthi, V. Tetrahedron: Asymmetry 2003, 14, 2839.
12. (a) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535.
13. (b) Ballemin-Loponnaz, S.; Tweddwl, J.; Ruble, J. C.; Breitting, F. M.; Gregory, C. Chem. Commun. 2000, 1009.
14. (a) Tiecco, M. In Topics in Current Chemistry: Organoselenium Chemistry: Modern Developments in Organic Synthesis; Wirth, T., Ed.; Electrophilic Selenium, Selenocyclizations; Springer-Verlag: Heidelberg, 2000; p 7.
15. (b) Organoselenium Chemistry - A Practical Approach; Back, T. G., Ed.; Oxford: New York, 2000.
16. (c) Wirth, T. Angew. Chem., Int. Ed. 2000, 39, 3742.
17. (d) Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Angew. Chem., Int. Ed. 2003, 42, 3131.
18. Tiecco, M.; Testaferri, L.; Santi, C.; Tomassini, C.; Marini, F.; Bagnoli, L.; Temperini, A. Chem. Eur. J. 2002, 8, 1118.
19. (a) Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988, 110, 1539.
20. (b) Lee, D.; Huh, E. A.; Kim, M.-J.; Jung, H. M.; Koh, J. H.; Park, J. Org. Lett. 2000, 15, 2377.
21. (c) Hideaki, R. Agric. Biol. Chem. 1987, 51, 3369.
22. Keck, G. E.; Wager, C. A. Org. Lett. 2000, 2, 2307.
23. (a) Back, T. G. In Organoselenium Chemistry; Liotta, D., Ed.; Electrophilic Selenium Reactions; Wiley: New York, 1987; p 1.
24. (b) Aprile, C.; Gruttadauria, M.; Amato, M. E.; D'anna, F.; Lo Meo, P.; Riela, S.; Noto, R. Tetrahedron 2003, 59, 2241.
25. (c) Cooper, M. A.; Ward, D. Tetrahedron 2004, 60, 7963.