Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts

Journal of Fluorine Chemistry

Volumn 97, Issue 1-2, 1999, Pages 51-55

  Ishii, Akihiro ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric catalysis; Fluoral; Friedel Crafts reaction; Vinyl ether

Indexed keywords

EID: 0001910527     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(99)00025-1     Document Type: Article

References (30)

1. I. Ojima, J.R. McCarthy, J.T. Welch (Eds.), Biomedical Frontiers of Fluorine Chemistry, American Chemical Society, 1996.
2. Resnati G. Tetrahedron. 49:1993;9385.
3. G. Resnati, V.A. Soloshonok (Eds.), Tetrahedron, 52 (1996) 1.
4. G.A. Olah, R.D. Chambers, G.K.S. Prakash, Synthetic Fluorine Chemistry, Wiley, New York, 1992.
5. Iseki K. Tetrahedron. 54:1998;13887.
6. Mikami K., Yajima T., Takasaki T., Matsukawa S., Terada M., Uchimaru T., Maruta M. Tetrahedron. 52:1996;85.
7. Mikami K., Yajima T., Terada M., Uchimaru T. Tetrahedron Lett. 34:1993;7591.
8. M.B. Smith, Organic Synthesis, McGraw-Hill, New York, 1994, p. 1313.
9. H. Heaney, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, vol. 2, Pergamon Press, Oxford, 1991, p. 733.
10. R.M. Roberts, A.A. Khalaf, Friedel-Crafts Alkylation Chemistry. A Century of Discovery, Dekker, New York, 1984.
11. G.A. Olah, Friedel-Crafts Chemistry, Wiley, New York, 1973.
12. Costa P.R.R., Cabral L.M., Alencar K.G., Schmidt L.L., Vasconcellos M.L.A.A. Tetrahedron Lett. 38:1997;7021.
13. El Kaim L., Guyoton S., Meyer C. Tetrahedron Lett. 37:1996;375.
14. Bigi F., Sartori G., Maggi R., Cantarelli E., Galaverna G. Tetrahedron: Asymmetry. 4:1993;2411.
15. M. Terada, N. Sayo, K. Mikami, Synlett (1995) 411.
16. Casiraghi G., Bigi F., Casnati G., Sartori G., Soncini P., Gasparri Fava G., Ferrari Belicchi M. J. Org. Chem. 53:1988;1779.
17. Erker G., van der Zeijden A.A.H. Angew. Chem. Int. Ed. Engl. 29:1990;512.
18. Bigi F., Casiraghi G., Casnati G., Sartori G., Gasparri Fava G., Ferrari Belicchi M. J. Org. Chem. 50:1985;5018.
19. A. Toshimitsu, C. Hirosawa, K. Tamao, Synlett (1996) 465.
20. Muehldorf A.V., Guzman-Perez A., Kluge A.F. Tetrahedron Lett. 35:1994;8755.
21. A. Ishii, V.A. Soloshonok, K. Mikami, J. Org. Chem., in press.
22. Mikami K., Matsukawa S. Nature. 385:1997;613.
23. Mikami K., Motoyama Y., Terada M. J. Am. Chem. Soc. 116:1994;2812.
24. Rummens F.H.A., de Haan J.W. Org. Magn. Res. 2:1970;351.
25. Dale J.A., Mosher H.S. J. Am. Chem. Soc. 95:1973;512.
26. Heathcock C.H., Pirrung M.C., Sohn J.E. J. Org. Chem. 44:1979;4294.
27. Hoffmann R.W. Chem. Rev. 89:1989;1841.
28. R. Schwesinger, J. Willaredt, in: G. Helmchen, R.W. Hoffmann, J. Mulzer, E. Schaumann (Eds.), Houben-Weyl E21, vol. 8, Thieme, Stuttgart, 1996.
29. Sharpless K.B., Verboeven T.R. Aldrichim. Acta. 12:1979;63.
30. Tan L., Chen C., Larsen R.D, Verhoeven T.R., Reider P.J. Tetrahedron Lett. 39:1998;3961.