Russian Journal of Organic Chemistry

, Volume 47, Issue 3, pp 371–373 | Cite as

Ionic liquid-phase organic synthesis (IoLiPOS) methodology applied to cross aldol reaction

  • H. Hakkou
  • D. Carrié
  • L. Paquin
  • J. -P. Bazureau
Article

Abstract

Cross aldol reaction in task-specific ionic liquids was developed. Ionic liquid-phase bound aldehyde reacted with various ketones (acetone, cyclopentanone, and butan-2-one) with l-proline as catalyst to afford various ionic liquid-phase supported aldols in yields ranging from 81 to 99%. Detachment of the aldol in MeOH was realized by transesterification using 15% of MeONa. The structure of intermediates in each step was verified by spectroscopic analysis.

Keywords

Ionic Liquid Aldol Cyclopentanone Aldol Reaction MeONa 

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References

  1. 1.
    Eder, U., Sauer, G., and Wieckert, R., Angew. Chem., Int. Ed. Engl., 1971, vol. 10, p. 496; Hajos, Z.G. and Parish, D.R., J. Org. Chem., 1974, vol. 39, p. 1615.CrossRefGoogle Scholar
  2. 2.
    Sakthivel, K., Notz, W., Bui, T., and Barbas, C.F., J. Am. Chem. Soc., 2001, vol. 123, p. 5260.CrossRefGoogle Scholar
  3. 3.
    Cordova, A., Zou, W., Dziedzic, P., Ibrahim, I., Reyes, E., and Xu, Y., Chem. Eur. J., 2006, vol. 12, p. 5383.CrossRefGoogle Scholar
  4. 4.
    Lee, S., Chem. Commun., 2006, p. 1049.Google Scholar
  5. 5.
    Fraga-Dubreuil, J., Famelart, M.H., and Bazureau, J.P., Org. Proc. Res. Dev., 2002, vol. 6, p. 374.CrossRefGoogle Scholar
  6. 6.
    Fraga-Dubreuil, J. and Bazureau, J.P., Tetrahedron Lett., 2001, vol. 42, p. 6097.CrossRefGoogle Scholar
  7. 7.
    Mia, W. and Chan, T.H., Acc. Chem. Res., 2006, vol. 39, p. 897.CrossRefGoogle Scholar
  8. 8.
    He, X. and Chan, T.H., Org. Lett., 2007, vol. 9, p. 2681.CrossRefGoogle Scholar
  9. 9.
    Ionic Liquids in Synthesis, Wasserscheid, P. and Welton, T., Eds., Weinheim: Wiley, 2003.Google Scholar
  10. 10.
    Legeay, J.C., Vanden Eynde, J.J., and Bazureau, J.P., Tetrahedron, 2008, vol. 64, p. 5328.CrossRefGoogle Scholar
  11. 11.
    Bazureau, J.P., Hamelin, J., Mongin, F., and Texier-Boullet, F., Microwaves in Organic Synthesis, Loupy, A., Ed., Weinheim: Wiley, 2006, 2nd ed., chap. 10, p. 426; Besson, T. and Brain, C.T., Microwave-Assisted Organic Synthesis; Tierney, J. and Lidström, P., Eds., Oxford UK: Blackwell, 2005, chap. 3.Google Scholar
  12. 12.
    Commarmot, R., Didenot, R., and Gardais, J.F., FR Patent Appl. no. 25 560 529, 1985; Chem. Abstr., 1986, vol. 105, no. 17 442.Google Scholar
  13. 13.
    Teck-Peng Loh, Li-Chun Feng, Hai-Yan Yang, and Jian-Ying Yang, Tetrahedron Lett., 2002, vol. 43, p. 8741.CrossRefGoogle Scholar
  14. 14.
    Houk, K.N. and Liot, B., Acc. Chem. Res., 2004, vol. 37, p. 487.CrossRefGoogle Scholar
  15. 15.
    Lombardo, M., Pari, F., Easwar, S., and Trombini, C., Adv. Synth. Catal., 2007, vol. 349, p. 2061.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • H. Hakkou
    • 1
  • D. Carrié
    • 1
  • L. Paquin
    • 1
  • J. -P. Bazureau
    • 1
  1. 1.Laboratoire Sciences Chimiques de Rennes, UMR CNRS 6226, Groupe Ingénierie Chimique & Molécules pour le Vivant (ICMV), Bât. 10A, Campus de BeaulieuUniversité de Rennes 1RENNES CedexFrance

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