Improvement on the synthesis of (E )-alk-3-enoic acids

Abstract

(E )-Alk-3-enoic acids have been prepared in high yield (85–90%) and excellent stereoselectivity (98–99%) by a modified Knoevenagel condensation of a straight carbon chain aldehyde with malonic acid, in dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) at 100 °C, in the presence of piperidinium acetate as catalyst. Condensation of the aldehyde with a monoester of malonic acid, under the above conditions, gave the corresponding ester of (E )-alk-3-enoic acid in high yield (76–82%) and good stereoselectivity (90–92%). Condensation of the aldehyde with cyanoacetic acid gave the β,γ-unsaturated nitrile in moderate yield (35–40%) without stereoselectivity.

References

1. Volatile Compounds in Food, Qualitative and Quantitative Data, ed. H. Maarse, C. A. Visscher and M. H. Boelens, TNO-CIVO Food Analysis Institut, Netherlands, 1989.
2. P. Schreier, F. Drawert and A. Junker, J. Agric. Food Chem., 1976, 24, 331.
3. G. R. Takeoda, R. A. Flath, M. Gunter and W. Jennings, J. Agric. Food Chem., 1988, 36, 553.
4. R. Naf-Muller and B. Willham, Helv. Chim. Acta, 1971, 54, 1880; K. E. Murray, J. Shipton and F. B. Whitfield, Aust. J. Chem., 1972, 25, 1921.
5. A. A. Cosse, J. L. Todd, J. G. Millar, L. A. Martinez and T. C. Baker, J. Chem. Ecol., 1995, 21, 1823.
6. R. Baker, R. H. Herbert and G. G. Grant, J. Chem. Soc., Chem. Commun., 1985, 824.
7. H. Fukui, F. Matsumura, M. C. Ma and W. E. Burkholder, Tetrahedron Lett., 1974, 3563.
8. M. Renou, Ch. Descoins, J. Y. Lallemand, E. Priesner, M. Lettere and M. Gallois, Z. Angew. Entomol., 1980, 90, 275.
9. E. E. van Tamelen and M. Shamma, J. Am. Chem. Soc., 1954, 76, 2315; J. Klein, J. Am. Chem. Soc., 1959, 81, 3611.
10. J. Malek and M. Cerny, Synthesis, 1972, 217.
11. J. M. Millar, A. C. Oehlschlager and J. W. Wong, J. Org. Chem., 1983, 48, 4404; G. H. Del Vecchio and A. C. Oehlschlager, J. Org. Chem., 1994, 59, 4853.
12. F. Camps, J. Coll, A. Guerrero, J. Guitart and M. Riba, Chem. Lett., 1982, 715.
13. R. R. Rando and W. E. Doering, J. Org. Chem., 1968, 33, 1671; O. Piva, F. Henin, J. Muzart and J. P. Pete, Tetrahedron Lett., 1987, 28, 4825.
14. T. Tsuboi, K. Muranaka, T. Sakai and A. Takeda, J. Org. Chem., 1986, 51, 4944; Y. Ikeda, J. Ukai, N. Ikeda and H. Yamamoto, Tetrahedron, 1987, 43, 743.
15. S. I. Murahashi, Y. Imada, Y. Taniguchi and S. Higashiura, J. Org. Chem., 1993, 58, 1538.
16. T. Sato, M. Takeuchi, T. Itoh, M. Kawashima and T. Fujisawa, Tetrahedron Lett., 1981, 19, 1817.
17. H. C. Brown, N. G. Bhat and J. B. Campbell, J. Org. Chem., 1986, 51, 3398.
18. M. Z. Deng, N. S. Li and V. Z. Huang, J. Org. Chem., 1992, 57, 4017.
19. J. R. Johnson, in Organic Reactions, ed. R. Adams, John Wiley and Sons, New York, 1967, vol 15, p. 204; R. P. Linstead and E. G. Noble, J. Chem. Soc., 1933, 557.
20. N. Ragoussis, Tetrahedron Lett., 1987, 28, 93.
21. L. J. Bellamy, The Infrared Spectra of Complex Molecules, John Wiley and Sons, New York, 1975, vol 1, pp. 54 and 59.
22. L. M. Jackman and S. Sternhell, in Application of NMR Spectroscopy in Organic Chemistry, ed D. H. R. Barton and W. Doering, Pergamon Press, Oxford, 1969, p. 301.
23. V. Ragoussis and V. Theodorou, Synthesis, 1993, 86.
24. J. Kennedy, N. J. McCorkindale and R. A. Raphael, J. Chem. Soc., 1961, 3813.
25. E. J. Corey, J. Am. Chem. Soc., 1952, 74, 5879; 1953, 75, 1163.
26. A. C. Cope, C. H. Hofmann, C. Wyckoff and E. Hardenbergh, J. Am. Chem. Soc., 1941, 63, 3452.
27. H. Yamanaka, M. Yokoyama, T. Sakamoto, T. Shiraishi, T. Sagi and M. Mizugaki, Heterocycles, 1983, 20, 1541.
28. J. Julliard, Recommended methods for purification of solvents, Pergamon press, Oxford, 1982, p. 34.
29. R. E. Strube, Org. Synth., 1964, Coll Vol. 4, 417.
30. J. A. Knight and J. H. Diamond, J. Org. Chem., 1959, 24, 400.
31. E. J. Corey and G. Fraenkel, J. Am. Chem. Soc., 1953, 75, 1168.
32. Beilsteins Handbuch der Organischen Chemie, Springer-Verlag, Berlin, Basic series, vol. 10, p. 520.