In the Claisen condensation, an ester enolate attacks an ester, with an alkoxide anion leaving subsequently to give a $\beta$-keto ester. Is it possible for a typical enolate of an aldehyde or ketone to react with an acid chloride (acting as the electrophile) to give a $\beta$-keto aldehyde or ketone, with the chloride ion leaving in a similar manner to how the alkoxide leaves in Claisen condensation?

Similarly, could I also extend it to the anhydride as well? Would we observe a similar Claisen-like mechanism?

  • $\begingroup$ It seems that an enamine is able to react in this fashion with an acid chloride: chemtube3d.com/Enamine_acylation.html $\endgroup$ – Tan Yong Boon Oct 31 '18 at 5:24
  • $\begingroup$ I think it is possible. $\endgroup$ – Soumik Das Oct 31 '18 at 9:29
  • $\begingroup$ Certainly possible if the enolate is generated with a non-nucleophilic base $\endgroup$ – Waylander Oct 31 '18 at 13:17

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