β-Nitroacrylates and silyl enol ethers as key starting materials for the synthesis of polyfunctionalized β-nitro esters and 1,2-oxazine-2-oxides

Tetrahedron

Volumn 65, Issue 15, 2009, Pages 2916-2920

  Ballini, Roberto ^a   Bosica, Giovanna ^a   Gabrielli, Serena ^a   Palmieri, Alessandro ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMMONIUM FLUORIDE; ESTER DERIVATIVE; ETHER DERIVATIVE; OXIDE; POLYFUNCTIONAL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 61549101568     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.009     Document Type: Article

References (37)

1. Perlmutter P. Conjugated Addition Reactions in Organic Synthesis (1992), Pergamon, Oxford
2. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley-VCH, NewYork, NY pp 70-103
3. Ballini R., Fiorini D., and Palmieri A. Tetrahedron Lett. 45 (2004) 7027
4. Ballini R., Fiorini D., and Palmieri A. Tetrahedron Lett. 46 (2005) 1245
5. Ballini R., Araújo-Bazán N., Bosica G., and Palmieri A. Tetrahedron Lett. 49 (2008) 3865
6. Ballini R., Gabrielli S., Palmieri A., and Petrini M. Tetrahedron 64 (2008) 5435
7. Nielsen A.T., and Archibald T.G. Tetrahedron 26 (1970) 3475
8. Miyashita M., Yanami T., and Yoshikoshi A. J. Am. Chem. Soc. 98 (1976) 4679
9. Daneo S., Pitacco G., Risaliti A., and Valentin E. Tetrahedron 38 (1982) 1499
10. Miyashita M., Yanami T., Kumazawa T., and Yoshikoshi A. J. Am. Chem. Soc. 106 (1984) 2149
11. Yoshikoshi A., and Miyashita M. Acc. Chem. Res. 18 (1985) 284
12. Varma R.S., and Kabalka G.W. Heterocycles 24 (1986) 2645
13. Denmark S.E., and Marcin L.R. J. Org. Chem. 58 (1993) 3857
14. Denmark S.E., and Marcin L.R. J. Org. Chem. 60 (1995) 3221
15. Denmark S.E., and Thorarensen A. Chem. Rev. 96 (1996) 137
16. Uittenbogaard R.M., Seerden J.-P.G., and Sheeren H.W. Tetrahedron 53 (1997) 11929
17. Denmark S.E., and Dixon J.A. J. Org. Chem. 63 (1998) 6178
18. Denmark S.E., and Hurd A.R. J. Org. Chem. 63 (1998) 3045
19. Kuster G.J., Kalmoua F., De Gelder R.H., and Scheeren W. Chem. Commun. (1999) 855
20. Denmark S.E., and Seierstad M. J. Org. Chem. 64 (1999) 1610
21. Avalos M., Babiano R., Cintas P., Higes F.J., Jiménez J.L., Palacios J.C., and Silva M.A. J. Org. Chem. 64 (1999) 1494
22. Benedetti F., Drioli S., Nitti P., Pitacco G., and Valentin E. Arkivoc (2001) 140
23. Denmark S.E., and Cottell J.J. In: Padwa A., and Pearson W.H. (Eds). The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (2002), Wiley-Interscience, New York, NY 83-167
24. Tsoungas P.G. Heterocycles 57 (2002) 1149
25. Seebach D., and Brook M.A. Helv. Chim. Acta 68 (1985) 319
26. Brook M.A., and Seebach D. Can. J. Chem. 65 (1987) 850
27. Seebach D., Lyapkalo I.M., and Dahinden R. Helv. Chim. Acta 82 (1999) 1829
28. Denmark S.E., and Xie M. J. Org. Chem. 72 (2007) 7050
29. Bellachioma G., Castrica L., Fringuelli F., Pizzo F., and Vaccaro L. Green Chem. 10 (2008) 327
30. Bakuzis P., Bakuzis M.L.F., and Weingartner T.F. Tetrahedron Lett. 19 (1978) 2371
31. Seebach D., Colvin E.W., and Lehr F. Chimia 1 (1979) 33
32. Miyakoshi T., Saito S., and Kumanotani J. Chem. Lett. (1981) 1677
33. Fuso R., and Rossi S. Chem. Ind. (London) (1957) 1650
34. Gelbart G. Synthesis (1977) 113
35. Ballini R., and Palmieri A. Adv. Synth. Catal. 348 (2006) 1154
36. Ballini R., Bosica G., Palmieri A., Petrini M., and Pierantozzi C. Tetrahedron 59 (2003) 7283
37. We tried to use, as source of fluoride, CsF or KF on basic alumina without any success.