Facile and highly stereoselective one-pot synthesis of either (E)- or (Z)-nitro alkenes

Organic Letters

Volumn 10, Issue 7, 2008, Pages 1449-1451

  Fioravanti, Stefania ^a   Pellacani, Lucio ^a   Tardella, Paolo A ^a   Vergari, Maria Cecilia ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 59849093323     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800224k     Document Type: Article

References (34)

1. (a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701-1716.
2. (b) Ballini, R.; Palmieri, A.; Fiorini, D. ARKIVOC 2007, 172-194.
3. (c) Almasi, D.; Alonso, D. A.; Najera, C. Tetrahedron: Asymmetry 2007, 18, 299-365.
4. (d) Bianchi, L.; Maccagno, M.; Petrillo, G.; Sancassan, F.; Spinelli, D.; Tavani, C. In Targets in Heterocyclic Systems: Chemistry and Properties; Attanasi, O. A., Spinelli, D., Eds.; Società Chimica Italiana: Rome, 2006; Vol. 10, pp 1-23.
5. (e) Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933-971.
6. (f) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877-1894.
7. (g) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 66, 751-762.
8. (a) Ballini, R.; Fiorini, D.; Maggi, R.; Oro, C.; Palmieri, A.; Sartori, G. Synlett 2006, 1849-1850.
9. (b) Lee, J. Y.; Hong, Y.-T.; Kim, S. Angew. Chem., Int. Ed. 2006, 45, 6182-6186.
10. (c) Ballini, R.; Barboni, L.; Fiorini, D.; Palmieri, A.; Petrini, M. ARKIVOC 2006, 127-152.
11. (d) Mendler, B.; Kazmaier, U. Org. Lett. 2005, 7, 1715-1718.
12. (a) Bhaduri, A. P. Synlett 1990, 557-564.
13. (b) Talalay, P.; De Long, M. J.; Prochaska, H. J. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8261-8265.
14. (c) Alston, T. A.; Porter, D. J. T.; Bright, H. J. Bioorg. Chem. 1985, 13, 375-403.
15. (d) Averbeck, D.; Averbeck, S.; Rene, L.; Buisson, J. P.; Royer, R. Eur. J. Med. Chem. 1980, 15, 539-544.
16. Henry, L. C. R. Hebd. Seances Acad. Sci. 1895, 120, 1265-1270.
17. Rewiews: (a) Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561-2574.
18. (b) Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron: Asymmetry 2006, 17, 3315-3326.
19. (c) Luzzio, F. A. Tetrahedron 2001, 57, 915-945.
20. (a) Hubner, J.; Liebscher, J.; Pätzel, M. Tetrahedron 2002, 58, 10485-10500.
21. (b) Kawai, Y.; Inaba, Y.; Tokitoh, N Tetrahedron: Asymmetry 2001, 12, 309-318.
22. (c) Lee, K.; Oh, D. Y. Synth. Commun. 1989, 19, 3055-3060.
23. (d) Knochel, P.; Seebach, D. Synthesis 1982, 1017-1018.
24. Hayama, T.; Tomoda, S.; Takeuchi, Y.; Nomura, Y. Tetrahedron Lett. 1982, 23, 4733-4734.
25. (a) Ono, N.; Kamimura, A.; Sasatani, H.; Kaji, A. J. Org. Chem. 1987, 52, 4133-4135.
26. (b) Ono, N.; Kamimura, A.; Kawai, T.; Kaji, A. Chem. Commun. 1987, 1550-1551.
27. (a) Fioravanti, S.; Marchetti, F.; Pellacani, L.; Ranieri, L.; Tardella, P. A. Tetrahedron: Asymmetry 2008, 19, 231-236.
28. (b) Fioravanti, S.; Pellacani, L.; Tardella, P. A.; Morreale, A.; Del Signore, G. J. Comb. Chem. 2006, 8, 808-811.
29. (c) Fioravanti, S.; Morreale, A.; Pellacani, L.; Tardella, P. A. Synlett 2004, 1083-1085.
30. Using a stoichiometric amount of piperidine, a complex mixture was obtained, in which it was not possible to detect either nitro alkenes or their precursors.
31. 2 at reflux failed.
32. Kawai, Y.; Inaba, Y.; Tokitoh, N. Tetrahedron: Asymmetry 2001, 12, 309-318.
33. For a different synthesis of (E)- and (Z)-7 see: Dumez, E.; Faure, R.; Dulcère, J.-P. Eur. J. Org. Chem. 2001, 2577-2588.
34. 1H NMR spectrum of the crude mixture.