Reactions of β-alkoxyvinyl trifluoromethyl ketones with terminal alkynes - Reagent-controlled regioselectivity addition reactions

Canadian Journal of Chemistry

Volumn 83, Issue 12, 2005, Pages 2127-2131

  Zhu, Shizheng ^a   Jin, Guifang ^a   Jiang, Hulling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkoxyvinyl trifluoromethyl ketones; 1,2 addition; 1,4 addition; Alkynes; Catalysts

Indexed keywords

CATALYSTS; FURAN RESINS; KETONES; REACTION KINETICS;

Β-ALKOXYVINYL TRIFLUOROMETHYL KETONES; 1,2-ADDITION; 1,4-ADDITION; ALKYNES;

ADDITION REACTIONS;

4 TRIFLUOROACETYL 2,3 DIHYDROFURAN; 5 TRIFLUOROACETYL 3,4 DIHYDRO 2H PYRAN; ALKYNE; BETA ALKOXYVINYL TRIFLUOROMETHYL KETONE; FURAN DERIVATIVE; KETONE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

ALKYNYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE;

EID: 33744473053     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-247     Document Type: Article

References (27)

1. (a) R.E. Banks, B.E. Smart, and J.C. Tatlow (Editors). Organofluorine chemistry, principles and commercial application. Plenum, New York. 1994;
2. (b) R. Filler, Y. Kobayashi, and L.M. Yagupolskii (Editors). Organofluorine compounds in medicinal chemistry and biomedical applications. Elsevier, Amsterdam. 1993;
3. J.P. Begue and D. Bonnet-Delpon. Tetrahedron, 47, 3207 (1991).
4. (a) W.S. Huang and C.Y. Yuan. J. Chem. Soc. Perkin Trans. 1, 741 (1995);
5. (b) A.V. Sanin, V.G. Nenajdenko, K.I. Smolko, D.I. Detrisenko, and E.S. Balenkova. Synthesis, 842 (1998);
6. (c) V.G. Nenajdenko, A.L. Krasovsky, M.V Lebedev, and E.S. Balenkova. Synlett, 1349 (1997);
7. (d) S.Z. Zhu, C.Y. Qin, G.L. Xu, Q.L. Chu, and Q.C. Huang. J. Fluorine Chem. 99, 141 (1999).
8. (a) V.G. Nenjdenko, A.V. Sanin, and E.S. Balenkova. Russ. Chem. Rev. 68, 437 (1999);
9. (b) M.W. Walter, R.M. Adlington, J.E. Baldwin, and C.J. Schofield. J. Org. Chem. 63, 5179 (1998).
10. (a) M. Kawase, H. Harada, S. Satio, J.M. Cui, and S. Tani. Biorg. Med. Chem. Lett. 9, 193 (1999);
11. (b) D.L. Boger, H. Sato, A.E. Lemet, B.J. Austin, J.E. Patterson, M.P. Patricelli, and B.F. Cravatt. Biorg. Med. Chem. Lett. 9, 265 (1999).
12. N.P. Gambaryan, L.A. Simonyan, and P.V. Petrovskii. Izv. Akad. Nauk SSSR Ser. Khim. 918 (1967).
13. (a) M. Hojo, R. Masuda, Y. Kokuryo, H. Shioda, S. Matsuo, and I.I. Gerus. Chem. Lett. 499 (1976);
14. (b) M.G. Gorbunova, S.I. Vdovenko, Y.L. Yagupolskii, and V.P. Kukhar. Zh. Org. Khim. 26, 1877 (1990);
15. (c) S.I. Vdovenko, I.I. Gerus, and M.G. Gorbunova. J. Chem. Soc. Perkin Trans. 1, 559 (1993);
16. (d) M.G. Gorbunova, I.I. Gerus, and V.P. Kukhar. J. Fluorine Chem. 65, 25 (1993);
17. (e) H.G. Bonacorso, I.S. Lopes, A.D. Wastowski, N. Zanatta, and M.A.P. Martins. J. Fluorine Chem. 120, 29 (2003).
18. R.J. Andrew and J.M. Mellor. Tetrahedron, 56, 7261 (2000).
19. S.Z. Zhu, G.L. Xu, C.Y. Qin, Q.L. Chu, and Y. Xu. Monatsh. Chem. 130, 671 (1999).
20. I.S. Kruchok, I.I. Gerus, and V.P. Kukhar. Tetrahedron, 56, 6533 (2000).
21. S.J. Coles, J.M. Mellor, A.H. El-Sagheer, E.E.M. Salem, and R.N. Metwally. Tetrahedron, 56, 10057 (2000).
22. (a) Q.L. Chu, L.P. Song, G.F. Jin, and S.Z. Zhu. J. Fluorine Chem. 108, 51 (2001);
23. (b) S.Z. Zhu, G.F. Jin, W.M. Peng, and Q.C. Huang. Tetrahedron, 59, 2899 (2003).
24. M. Yamaguchi, A. Hayashi, and M. Hirama. Chem. Lett. 2479 (1992);
25. N.K. Anand and E.M. Carreira. J. Am. Chem. Soc. 123, 9687 (2001).
26. B. Jiang and Y.G. Si. Tetrahedron Lett. 43, 8323 (2002).
27. M.A.R. Martins, D.J. Emmerich, C.M.P. Pereira, W. Cunico, M. Rossato, N. Zanatta, and H.G. Bonacorso. Tetrahedron Lett. 45, 4935 (2004).