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Updated: Jun 21, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Gold(I)-catalyzed cascade cyclization of allenyl epoxides
Michael A Tarselli1, J Lucas Zuccarello, Stephen J Lee
1Caudill Laboratories, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
Abstract:
Cationic gold(I) phosphite catalysts activate allenes for epoxide cascade reactions. The system is tolerant of numerous functional groups (sulfones, esters, ethers, sulfonamides) and proceeds at room temperature in dichloromethane. The cyclization pathway is sensitive to the substitution pattern of the epoxide and the backbone structure of the A-ring. It is capable of producing medium-ring ethers, fused 6-5 bicyclic, and linked pyran-furan structures. The resulting cycloisomers are reminiscent of structures found in numerous polyether natural products.
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