Cyclization of Enynes

By: William Sommer, ChemFiles Volume 9 Article 5

The cyclization of enynes utilizes the nucleophilicity of alkenes to react with alkynes.1 The reaction stemmed from the investigations of Fukuda and Utimoto of the gold-catalyzed hydroamination of alkynes.2 The authors noticed that water and alcohols reacted as nucleophiles with alkynes in the presence of a gold catalyst. Stemming from this observation, reports flourished on the use of gold to catalyze the reaction of alkenes with alkynes. This new gold-catalyzed reaction is mainly used to synthesize cyclic compounds allowing access to important synthons in a few steps.



  1. (a) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (b) Jiménez-Núñez, E. et al. Chem. Commun. 2007, 333. (c) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2006, 45, 7896.
  2. Fukuda, Y. et al. Synthesis 1991, 975.



Related Links