Crossed Claisen and Dieckmann

Under construction

This page is a draft outline. It is visible to admins and still needs a full lesson.

The existing Claisen page is the self-condensation. These are the two variants students need for synthesis.

  • Crossed Claisen: one ester has no α hydrogen, so only one enolate can form. Predict the β-keto ester.
  • What goes wrong if both esters are enolizable.
  • Dieckmann condensation: an intramolecular Claisen of a diester, giving a cyclic β-keto ester.
  • Ring size: five- and six-membered rings form readily.
  • Retrosynthesis: seeing a cyclic β-keto ester and disconnecting it to a diester.