(Z)-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl-Ene Reaction.
Pathan Mosim AminQi CuiShaozhong WangZhi-Xiang YuPublished in: Organic letters (2021)
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.
Keyphrases
- room temperature
- density functional theory
- reduced graphene oxide
- randomized controlled trial
- metal organic framework
- ionic liquid
- molecular dynamics
- silver nanoparticles
- molecular dynamics simulations
- sensitive detection
- molecular docking
- visible light
- electron transfer
- gold nanoparticles
- monte carlo
- crystal structure