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Catalyzed Tandem Reaction of 3-Silyloxy-1,5-enynes Consisting of Cyclization and Pinacol Rearrangement


  • This project was supported by the Deutsche Forschungsgemeinschaft (DFG) and the Fonds der Chemischen Industrie (FCI). We thank Olaf Ackermann for assistance with HPLC. We thank Prof. Thorsten Bach and his group for helpful discussions and generous support.


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Au-spicious! Under silver-free conditions, simple 3-silyloxy-1,5-enynes were converted into complex cyclopentenes by a gold(I)-catalyzed sequence that likely proceeds through a carbocyclization followed by a pinacol rearrangement. For the final demetalation step, isopropyl alcohol and N-iodosuccinimide are effectively utilized, and the resulting products are set up for a wealth of further reactions.

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