(Z)-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl–Ene Reaction

Amin, Pathan Mosim; Cui, Qi; Wang, Shaozhong; Yu, Zhi-Xiang

(Z)-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl–Ene Reaction

2021

Amin, Pathan Mosim | Cui, Qi | Wang, Shaozhong | Yu, Zhi-Xiang

A bimetallic protocol has been developed to construct (Z)-γ-alkylidenebutenolide compounds from readily available propargyl α-ketoesters. It involves a gold-catalyzed 1,3-acyloxy migration of propargyl α-ketoesters and a carbonyl-ene cyclization of in situ generated allenyl esters. DFT calculations suggest that the copper salt might play dual roles as both chloride abstractor facilitating the generation of highly active gold catalyst and Lewis acid promoting the stepwise intramolecular carbonyl-ene reaction.

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