• This reaction features a rare example of an OH- leaving group.
  • One can perform crossed aldol reactions on malonates without using a strong base to form an enolate. This reaction is difficult to stop however.
  • Firstly the aldol is formed, then reaction proceeds to show the formation of the dehydrated product.
  • The final stage of this reaction (formation of the dehydrated product) occurs via the E1cB mechanism.
  • This is a more controlled aldol reaction than its acid catalysed alternative.
  • This reaction can occur intramolecularly, within a single molecule.


  • References:
  • White J.D.; Blakemore P.R.; Green N.J.; et al., J. Org. Chem., 2002, Volume 67, No. 22, 7750-7760
  • Wei H.-X.; Hu J.; Purkiss D. W.; Paré P. W.; Tetrahedron Lett., 2003, Volume 44, Issue 5, 949