A short synthesis of conjugated unsaturated amides and esters via triphenylphosphine-catalysed isomerisation of acetylenic pentafluorophenyl esters†

Abstract

Isomerisation of acetylenic pentafluorophenyl esters in the presence of phosphines gives rise to activated dienoic acids, which can be coupled directly with amines and alcohols in a simple one-pot procedure.

References

1. G. Habermehl and P. Hammann, Naturstoffchemie, Springer, Berlin, 1992.
2. U. Gräfe, Biochemie der Antibiotika, Spektrum, Heidelberg, 1992.
3. F. VanMiddlesworth, C. Dufrese, J. Smith and K. E. Wilson, Tetrahedron, 1991, 47, 7563; Y. Doi, M. Ishibashi and J. Kobayashi, Tetrahedron, 1994, 50, 8651; J. E. Hochlowski, D. N. Whittern, A. Buko, L. Alder and J. B. McAlpine, J. Antibiot., 1995, 48, 614.
4. P. Traxler, J. Gruner and J. A. L. Auden, J. Antibiot., 1977, 30, 289; A. G. M. Barrett, M. Pena and J. A. Willardsen, J. Chem. Soc., Chem. Commun., 1995, 1145.
5. F. M. Arcamone, C. Bertazzoli, M. Ghione and T. G. Scotti, Microbiol., 1959, 7, 207.
6. F. Bohlmann and C. Zdero, Chem. Ber., 1973, 106, 1328.
7. A. Fredenhagen, S. Y. Tamura, P. T. M. Kenny, H. Komura, Y. Naya, K. Nakanishi, K. Nishiyama, M. Sugiura and H. Kita, J. Am. Chem. Soc., 1987, 109, 4409; J. Needham, M. T. Kelly, M. Ishige and R. J. Andersen, J. Org. Chem., 1994, 59, 2058.
8. R. Myokei, A. Sakurai, C. Chang, Y. Kodaira, N. Takahasi and S. Tamura, Tetrahedron Lett., 1969, 9, 695; M. Oka, Y. Nishiyama, S. Ohta, H. Kamei, M. Konishi, T. Miyaki, T. Oki and H. Kawaguchi, J. Antibiot., 1988, 41, 1331; H. Koshino, H. Osada, T. Yano, J. Uzawa and K. Isono, Tetrahedron Lett., 1991, 32, 7707.
9. K. Tanaka, M. Terauchi and A. Kaji, Chem. Lett., 1981, 315 and references cited therein T. Mandai, T. Moriyama, K. Tsujimoto, M. Kawada and J. Otera, Tetrahedron Lett., 1986, 27, 603.
10. J. Singh, K. L. Dhar and C. K. Atal, Tetrahedron Lett., 1969, 4975.
11. D. Seebach, H. Chow, R. F. W. Jackson, K. Lawson, M. A. Sutter, S. Thaisrivongs and J. Zimmermann, J. Am. Chem. Soc., 1985, 107, 5292; U. Schmidt, A. Kleefeldt and R. Mangold, J. Chem. Soc., Chem. Commun., 1992, 1687; R. W. Armstrong, Tetrahedron Lett., 1994, 35, 7743.
12. N. Lewis, P. W. McKeu and R. J. K. Taylor, Synlett, 1992, 898; F. Babudri, V. Fiandanese, F. Naso and A. Punzi, Tetrahedron Lett., 1994, 35, 2067; A. G. M. Barrett, M. Pena and J. A. Willardsen, J. Chem. Soc., Chem. Commun., 1995, 1145.
13. B. M. Trost and T. Schmidt, J. Am. Chem. Soc., 1988, 110, 2301; D. Ma, Y. Lin, X. Lu and Y. Lu, Tetrahedron Lett., 1988, 29, 1045; D. Ma, Y. Lu and X. Lu, J. Org. Chem., 1989, 54, 1105.
14. B. M. Trost and U. Kazmaier, J. Am. Chem. Soc., 1992, 114, 7933.
15. C. Guo and X. Lu, J. Chem. Soc., Chem. Commun., 1993, 394; C. Guo and X. Lu, J. Chem. Soc., Perkin Trans. 1, 1993, 1921.
16. S. D. Rychnovsky and J. Kim, J. Org. Chem., 1994, 59, 2659.
17. B. M. Trost and C. Li, J. Am. Chem. Soc., 1994, 116, 10819; C. Zhang and X. Lu, J. Org. Chem., 1995, 60, 2906; C. Zhang and X. Lu, Synlett, 1995, 645; K. Liou and C. Cheng, J. Chem. Soc., Chem. Commun., 1995, 1603.
18. U. Schmid, A. Lieberknecht, H. Griesser and J. Talbiersky, J. Org. Chem., 1982, 47, 3261.
19. D. Seebach, A. Thaler, D. Blaser and S. Y. Koo, Helv. Chim. Acta, 1991, 74, 1102.
20. S. Nahm and S. M. Weinreb, Tetrahedron Lett., 1991, 22, 3815.