Skip to main content
SpringerLink
Log in

New reactions of α-allylation of CH-acids with carbonyl groups

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

New α-allylation reactions were performed of CH-acids with carbonyl groups (β-ketoacetic esters, phenylacetone, β-tetralone, ethyl acetate and its α-substituted derivatives) using as deprotonating reagents depending on the substrate acidity sodium hydride, potassium tert-butilate, and sodium bis(trimethylsilyl)-amide. BrCH2CH=CRR′ (R= R′ = H, Me; R = Me, R′ = CH2Ph, CH2CH2Ph) and BrCH2CH=X (X = cyclohexanylidene, 4-pyranylidene, 4-N-Boc-piperidinylidene) were applied as allylating agents.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Jonczyk, F., Serafin, B., and Makosza, M., Roczniki Chem., 1971, vol. 45, p. 1027.

    CAS  Google Scholar 

  2. Cuvigny, T. and Julia, M., J. Organometal. Chem., 1987, vol. 331, p. 121.

    Article  CAS  Google Scholar 

  3. Antonioletti, R., Bonadies, F., Orelli, R., and Scettri, A., Gazz. Chim. Ital., 1992, vol. 122, p. 237.

    CAS  Google Scholar 

  4. Brindaban, C.R. and Sanjay, B., J. Chem. Soc. Perkin Trans. 1, 1992, p. 365.

    Google Scholar 

  5. Aranda, A., Diaz, A., Diez-Barra, E., de la Hoz, A., Moreno, A., Sánchez-Verdú, P., J. Chem. Soc. Perkin Trans. 1, 1992, p. 2427.

    Google Scholar 

  6. Queignec, R., Kirschleger, B., Lambert, F., and Aboutaj, M., Synth. Comm., 1988, vol. 18, p. 1213.

    Article  CAS  Google Scholar 

  7. Kryshtal, G.V., Zhdankina, G.M., and Zlotin, S.G., Russ. Chem. Bull., 2004, vol. 53, p. 652.

    Article  CAS  Google Scholar 

  8. Miguel, P.-L., Montserrat, M., Sarandeses, L.A., and Sestelo, J.P., J. Org. Chem., 2010, vol. 75, p. 5337.

    Article  Google Scholar 

  9. Tadigoppula, N., Satinath, S., Kandikonda, R., and Sriniwas, T., Org. Lett., 2011, vol. 13, p. 6140.

    Article  Google Scholar 

  10. Jolly, P.W. and Kokel, N., Synthesis, 1990, p. 771.

    Google Scholar 

  11. Safi, M. and Sinou, D., Tetrahedron Lett., 1991, vol. 32, p. 2025.

    Article  CAS  Google Scholar 

  12. Zhang, S.-W., Mitsudo, T., Kondo, T., and Watanabe, Y., J. Organometal. Chem., 1993, vol. 450, p. 197.

    Article  CAS  Google Scholar 

  13. Blart, E., Genet, J.P., Safi, M., Savignac, M., and Sinou, D., Tetrahedron, 1994, vol. 50, p. 505.

    Article  CAS  Google Scholar 

  14. Baruah, J. and Samuelson, A.G., New J. Chem., 1994, vol. 18, p. 961.

    CAS  Google Scholar 

  15. Uozumi, Y., Danjo, H., and Hayashi, T., Tetrahedron Lett., 1997, vol. 38, p. 3557.

    Article  CAS  Google Scholar 

  16. Feuerstein, M., Laurenti, D., Doucet, H., and Santelli, M., Synthesis, 2001, p. 2320.

    Google Scholar 

  17. Ozawa, F., Okamoto, H., Kawagishi, S., Yamamoto, S., Minami, T., Yoshifuji, M., J. Am. Chem. Soc., 2002, vol. 124, p. 10968.

    Article  CAS  Google Scholar 

  18. Akiyama, R. and Kobayashi, S., J. Am. Chem. Soc., 2003, vol. 125, p. 3412.

    Article  CAS  Google Scholar 

  19. Mitsudome, T., Nose, K., Mori, K., Mizugaki, T., Ebitani, K., Kitsukawa, K., and Kaneda, K., Angew. Chem. Int. Ed., 2007, vol. 46, p. 3288.

    Article  CAS  Google Scholar 

  20. Lin, S., Song, Ch.-X., Cai, G.-X., Wang, W.-H., Shi, Z.-J., J. Am. Chem. Soc., 2008, vol. 130, p. 12901.

    Article  CAS  Google Scholar 

  21. Patil, N.T. and Yamamoto, Y., Tetrahedron Lett., 2004, vol. 45, p. 3101.

    Article  CAS  Google Scholar 

  22. Breuilles, P. and Uguen, D., Tetrahedron Lett., 1990, vol. 31, p. 357.

    Article  CAS  Google Scholar 

  23. Joseph, P.M. and Mluleki, M.N., Tetrahedron, 1990, vol. 46, p. 2549.

    Article  Google Scholar 

  24. Saha, P., Bhunia, A., and Saikia, A.K., Org. Biomol. Chem., 2012, vol. 10, p. 2470.

    Article  CAS  Google Scholar 

  25. Tummatorn, J., Ruchirawat, S., and Ploypradith, P., Chem. Eur. J., 2010, vol. 16, p. 1445.

    Article  CAS  Google Scholar 

  26. Bruecher, O., Bergstraesser, U., Kelm, H., Hartung, J., Greb, M., Svoboda, I., and Fuess, H., Tetrahedron, 2012, vol. 68, p. 6968.

    Article  CAS  Google Scholar 

  27. Li, X.-W., Herrmann, J., Zang, Y., Grellier, P., Prado, S., Mueller, R., and Nay, B., Beilshtein J. Org. Chem., 2013, vol. 9, p. 1551.

    Article  Google Scholar 

  28. Moskalenko A.I. and Boev, V.I., Russ. J. Org. Chem., 2014, vol. 50, p. 953.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lipetsk Pedagogic State University, Lipetsk, Russia

    A. I. Moskalenko

  2. Russian State Agricultural University — Timiryazev MAA, Timiryazevskaya ul. 49, Moscow, 127550, Russia

    V. I. Boev

Authors
  1. A. I. Moskalenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Boev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. I. Boev.

Additional information

Original Russian Text © A.I. Moskalenko, V.I. Boev, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 181–186.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Moskalenko, A.I., Boev, V.I. New reactions of α-allylation of CH-acids with carbonyl groups. Russ J Org Chem 51, 167–173 (2015). https://doi.org/10.1134/S1070428015020049

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015020049

Keywords

Search

Navigation