β-Nitro acrylic esters as precursors for the one pot synthesis of polyfunctionalized α,β-unsaturated esters

Tetrahedron Letters

Volumn 46, Issue 8, 2005, Pages 1245-1246

  Ballini, Roberto ^a   Fiorini, Dennis ^a   Palmieri, Alessandro ^a  

^a Dipto di Sci Chimiche dell'Univ   (Italy)

Author keywords

, Unsaturated esters; Nitro acrylic esters; Michael addition; Nitrous acid elimination; Tandem process

Indexed keywords

ACETONITRILE; BASE; CARBENE; ESTER DERIVATIVE; NITRO DERIVATIVE; POLYFUNCTIONAL GROUP;

ARTICLE; CONJUGATE; ELECTRON; ELIMINATION REACTION; MICHAEL ADDITION; PRECURSOR;

EID: 13244251122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.009     Document Type: Article

References (25)

1. E.J. Corey, and X.-M. Cheng The Logic of Chemical Synthesis 1989 John Wiley and Sons New York
2. T.L. Ho Tactis of Organic Synthesis 1994 Wiley New York
3. B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford
4. J. Ap Simon The Total Synthesis of Natural Products 1998 John Wiley and Sons New York
5. J.R. Hwu, G.H. Hakimelahi, and C.T. Chou Tetrahedron Lett. 33 1992 6469
6. P. Galatsis, and D.J. Parks Tetrahedron Lett. 35 1994 6611
7. A.C. Cope, and C.M. Hoffman J. Am. Chem. Soc. 63 1941 3456
8. A. Galat J. Am. Chem. Soc. 68 1946 376
9. R.L. Shriner Org. React. 1 1947 1
10. C.R. Hauser, and D.S. Breslow Org. Synth. Coll. 3 1955 408
11. K.L. Rinehart, and E. Perkins Org. Synth. Coll. 4 1963 444
12. W.S. Wadsworth, and W.D. Emmons J. Am. Chem. Soc. 83 1961 1733
13. W.S. Wadsworth Org. React. 25 1977 73
14. W.S. Wadsworth Acc. Chem. Res. 16 1983 1411
15. B.E. Marynoff, and A.B. Reitz Chem. Rev. 89 1989 863
16. C. Shin, Y. Yonezawa, H. Narukawa, K. Nanjo, and J. Yoshimura Bull. Chem. Soc. Jpn. 45 1972 3595
17. R. Ballini, D. Fiorini, and A. Palmieri Tetrahedron Lett. 45 2004 7027
18. 4 filtered and concentrated under vacuum to give the crude compound 4, which was purified by flash chromatography (EtOAc/cyclohexane)
19. J.R. Wiseman J. Org. Chem. 29 1964 2793
20. M. Yamaguchi, M. Tsukamoto, S. Tanaka, and I. Hirao Tetrahedron Lett. 25 1984 5661
21. H. Boumchita, M. Legraverend, and E. Bisogni Heterocycles 32 1991 1785
22. E. Lee-Ruff, W.-Q. Wan, and J.-L. Jiang J. Org. Chem. 59 1994 2114
23. G.A. Molander, M.S. Quirmbach, L.F. Silva, K.C. Spencer, and J. Balsells Org. Lett. 3 2001 2257
24. H. Jayasuriya, G.F. Bills, C. Cascales, D.L. Zink, M.A. Goez, R.S. Jenkins, K.C. Silverman, R.B. Lingham, and S.B. Singh Bioorg. Med. Chem. Lett. 6 1996 2081
25. M.H. Benn, S.D. Lorimer, and N.B. Perry Phytochemistry 47 1998 1649