Skip to main content
SpringerLink
Log in

Base-catalyzed aldol- and Michael-type condensations in aqueous media

  • Chapter
Organic Synthesis in Water

Abstract

The aldol reaction is one of the most important ways to construct carbon-carbon bonds in organic synthesis. Nature itself seems to prefer this reaction in its biosynthetic processes, for example, in the prebiotic formation of saccharides [1]. Strictly speaking, the aldol reaction is the self-coupling of an aldehyde, having at least one active hydrogen in the α-position, to give a β-hydroxyaldehyde called an aldol (aldol addition), which sometimes dehydrates (aldol condensation).

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Decker, P.; Schweer, H., Origins of Life, 1984, 14, 335; (b) Decker, P.; Schweer, H.; Pohlmann, R.J., Chromatography, 1982, 244, 281; (c) Harsch, G.; Bauer, H.; Voelter, W., Liebigs Ann. Chem., 1984, 623.

    Article  CAS  Google Scholar 

  2. Mukaiyama, T.; Banno, K,; Narasaka, K., J. Am. Chem. Soc., 1974, 96, 7503.

    Article  CAS  Google Scholar 

  3. Kobayashi, S., Synlett, 1994, 689.

    Google Scholar 

  4. Yamamoto, Y.; Maruyama, K.; Matsumoto, K., J. Am. Chem. Soc., 1983, 105, 6963.

    Article  CAS  Google Scholar 

  5. Lubineau, A., J. Org. Chem., 1986, 51, 2142; (b) Lubineau, A.; Meyer, E., Tetrahedron, 1988, 44, 6065.

    Article  CAS  Google Scholar 

  6. Fringuelli, F.; Pani, G.; Piermatti, O.; Pizzo, F., Tetrahedron, 1994, 50, 11499; (b) Fringuelli, F.; Pani, G.; Piermatti, O.; Pizzo, F., Life Chem. Rep., 1995, 13, 133.

    Article  CAS  Google Scholar 

  7. Nivalkar, K.R.; Mudaliar, C.D.; Mashraqui, S.H., J. Chem. Res. (S), 1992, 98.

    Google Scholar 

  8. Sadvilcar, V.G.; Samant, S.D.; Gaikar, V.G., J. Chem. Tech. Biotechnol., 1995, 62, 405.

    Article  Google Scholar 

  9. Buonora, P.T.; Rosauer, K.G.; Dai, L., Tetrahedron Lett., 1995, 36, 4049.

    Article  Google Scholar 

  10. Watanabe, K.; Yamada, Y.; Goto, K., Bull. Chem. Soc. Jpn., 1985, 58, 1401.

    Article  CAS  Google Scholar 

  11. Zhang, Y.; Xu, W., Synth. Commun., 1989, 19, 1291.

    Article  CAS  Google Scholar 

  12. Desper, J.M.; Breslow, R., J. Am. Chem. Soc., 1994, 116, 12081.

    Article  CAS  Google Scholar 

  13. Denmark, S.E.; Lee, W., Tetrahedron Lett., 1992, 33, 7729.

    Article  CAS  Google Scholar 

  14. Brufola, G.; Fringuelli, F.; Piermatti, O.; Pizzo, F., Heterocycles, 1996, 43, 1257.

    Article  CAS  Google Scholar 

  15. Nakano, Y.; Niki, S.; Kinouchi, S.; Miyamae, H.; Igarashi, M., Bull. Chem. Soc. Jpn., 1992, 65, 2934.

    Article  CAS  Google Scholar 

  16. Sadvilkar, V.G.; Khadilkar, B.M.; Gaikar, V.G., J. Chem. Tech. Biotechnol., 1995, 63, 33.

    Article  CAS  Google Scholar 

  17. Khadilkar, B.M.; Gaikar, V.G.; Chitnavis, A.A., Tetrahedron Lett., 1995, 36, 8083.

    Article  CAS  Google Scholar 

  18. Kool, E.T.; Breslow, R., J. Am. Chem. Soc., 1988, 110, 1596.

    Article  CAS  Google Scholar 

  19. Augé, J.; Lubin, M.; Lubineau, A., Tetrahedron Lett., 1994, 35, 7947.

    Google Scholar 

  20. Shigemasa, Y.; Yokoyama, K.; Sashiwa, H.; Saimoto, H., Tetrahedron Lett., 1994, 35, 1263.

    Article  CAS  Google Scholar 

  21. Ben Ayed, T.; Amri, H., Synth. Commun., 1995, 25, 3813.

    Article  CAS  Google Scholar 

  22. Coitiño, E.L.; Tomasi, J.; Ventura, O.N., J. Chem. Soc., Faraday Trans., 1994, 90, 1745.

    Article  Google Scholar 

  23. Weiss, U.; Edwards, J.M., Tetrahedron Lett., 1968, 4885.

    Google Scholar 

  24. Yang-Lan, S.; Mueller-Johnson, M.; Oehldrich, J.; Wichman, D.; Weiss, U.; Cook, J.M., J. Org Chem., 1976, 41, 4053.

    Article  CAS  Google Scholar 

  25. Mitschka, R.; Oehldrich, J.; Takahashi, K.; Cook, J.M.; Weiss, U.; Silverton, J.V., Tetrahedron, 1981, 37, 4521.

    Article  CAS  Google Scholar 

  26. Deslongchamps, G.; Mink, D.; Boyle, P.D.; Singh, N., Can. J. Chem., 1994, 72, 1162.

    Article  CAS  Google Scholar 

  27. Fu, X.; Cook, J.M.; Aldrichim. Acta, 1992, 25, 43.

    CAS  Google Scholar 

  28. Gupta, A.K.; Fu, X.; Snyder, J.P.; Cook, J.M., Tetrahedron, 1991, 47, 3665.

    Article  CAS  Google Scholar 

  29. Detert, H.; Lanter, J.C.; Paquette, L.A., J. Org. Chem., 1995, 60, 353.

    Article  CAS  Google Scholar 

  30. Corsico Coda, A.; Desimoni, G.; Righetti, P.; Tacconi, G., Gazz. Chim. Ital., 1984, 114, 417.

    Google Scholar 

  31. Ranu, B.C.; Bahar, S., Tetrahedron, 1992, 48, 1327.

    Article  CAS  Google Scholar 

  32. Ballini, R., Synthesis, 1993, 687.

    Google Scholar 

  33. Van Westrenen, J.; Roggen, R.M.; Hoefnagel, M.A.; Peters, J.A.; Kieboom, A.P.G.; Van Bekkum, H., Tetrahedron, 1990, 46, 5741.

    Article  Google Scholar 

  34. Kryshtal, G.V.; Kulganeck, V.V.; Kucherov, V.F.; Yanovskaya, L.A., Synthesis, 1979, 107.

    Google Scholar 

  35. Antonioletti, R.; Bonadies, F.; Monteagudo, E.S.; Scettri, A., Tetrahedron Lett., 1991, 32, 5373.

    Article  CAS  Google Scholar 

  36. Boyer, J.; Corriv, R.J.P.; Perz, R.; Réyé, C., J. Chem. Soc., Chem. Commun., 1981, 122.

    Google Scholar 

  37. Lubineau, A.; Augé, J., Tetrahedron Lett., 1992, 33, 8073.

    Article  CAS  Google Scholar 

  38. Lubineau, A.; Bouchain, G.; Queneau, Y., J. Chem. Soc. Perkin Trans. 1, 1995, 2433.

    Article  Google Scholar 

  39. Bassetti, M.; Cerichelli, G.; Floris, B, Gazz. Chim. Ital., 1991, 121, 527.

    CAS  Google Scholar 

  40. Sakuraba, H.; Tananoka, Y.; Toda, F., J. Incl. Phenom. Mol. Recogn. Chem., 1991, 11, 195.

    Article  CAS  Google Scholar 

Download references

Authors
  1. F. Fringuelli
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. Piermatti
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. Pizzo
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Thomson Science

About this chapter

Cite this chapter

Fringuelli, F., Piermatti, O., Pizzo, F. (1998). Base-catalyzed aldol- and Michael-type condensations in aqueous media. In: Organic Synthesis in Water. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4950-1_7

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-4950-1_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7514-0410-4

  • Online ISBN: 978-94-011-4950-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation