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Imidazolidinone-Derived Enamines: Nucleophiles with Low Reactivity


  • We thank the Alexander von Humboldt Foundation (research fellowship for S.L.) and the Deutsche Forschungsgemeinschaft (SFB 749) for financial support, Dr. P. Mayer for the determination of the X-ray structures, and Dr. A. R. Ofial and Dr. M. Horn for helpful discussions.


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Extraordinarily weak nucleophiles: Enamines derived from imidazolidinones are 103–105 times less reactive than those derived from the Hayashi–Jørgensen catalyst. This finding explains the lower activity of MacMillan catalysts for enamine-activated reactions.