Reaction of α,β-unsaturated trifluoromethyl ketones with ethyl cyanoacetate

Research paper by V. G. Nenaidenko, S. V. Druzhinin, E. S. Balenkova

Indexed on: 03 Jun '08Published on: 03 Jun '08Published in: Russian Journal of Organic Chemistry


β-Aryl-substituted α,β-unsaturated trifluoromethyl ketones react with ethyl cyanoacetate to give the corresponding Michael addition products, ethyl 3-aryl-2-cyano-6,6,6-trifluoro-5-oxohexanoates, which are formed as mixtures of two diastereoisomers. The reaction time and product yield depend on electron-donating properties of the substituent in the initial ketone. The reaction is not accompanied by intramolecular cyclization of the Michael adducts.