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Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes

Multidisciplinary Digital Publishing Institute
Publication Date
  • α
  • β-Unsaturated Ketones
  • Pyrrolidine
  • 1-Methyl-4-Piperidone
  • Mannich-Elimination Sequence
  • Claisen-Schmidt Condensation


An efficient method for the facile synthesis of (E)-monoarylidene derivatives of homo- and heterocyclic ketones with various aldehydes in the presence of a pyrrolidine organocatalyst has been achieved. A range of α,β-unsaturated ketones were obtained in moderate to high yields (up to 99%). Unlike the Claisen-Schmidt condensation process, the formation of undesired bisarylidene byproducts is not observed. The possible reaction mechanism suggests that the reaction proceeds via a Mannich-elimination sequence.

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