Gold(I)-Catalyzed 5-endo Hydroxy- and Alkoxycyclization of 1,5-Enynes: Efficient Access to Functionalized Cyclopentenes


  • The authors thank Prof. S. Z. Zard and Dr. I. Hanna for helpful discussions and Rhodia Chimie Fine for a gift of HNTf2.


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The rapid and stereoselective construction of highly functionalized cyclopentenes is possible through gold(I)-catalyzed 5-endo hydroxy- and methoxycyclizations of 1,5-enynes. More complex 5,7- and 5,8-fused bicyclic structures of a type found in many terpene natural products can be formed by combining the cyclization reaction with ring-closing metathesis (RCM; see scheme).