Issue 4, 2023

Synthesis of α-pyrones via gold-catalyzed cycloisomerization/[2 + 1] cycloaddition/rearrangement of enyne-amides and sulfur ylides

Abstract

A novel gold-catalyzed cycloisomerization/[2 + 1]cycloaddition/[1,3]-sigmatropic rearrangement sequence of readily available acyclic enyne-amides and sulfur ylides is reported. This strategy enables rapid and efficient construction of a series of α-pyrone derivatives with diverse substituents. Based on several control experiments, a possible mechanism was also proposed to rationalize the cascade process.

Graphical abstract: Synthesis of α-pyrones via gold-catalyzed cycloisomerization/[2 + 1] cycloaddition/rearrangement of enyne-amides and sulfur ylides

Supplementary files

Article information

Article type
Research Article
Submitted
01 Sep 2022
Accepted
29 Dec 2022
First published
10 Jan 2023

Org. Chem. Front., 2023,10, 916-922

Synthesis of α-pyrones via gold-catalyzed cycloisomerization/[2 + 1] cycloaddition/rearrangement of enyne-amides and sulfur ylides

J. Yu, X. Wang, M. Xu, B. Zhang, Z. Xiong, H. Mao, X. Lv and L. Zhou, Org. Chem. Front., 2023, 10, 916 DOI: 10.1039/D2QO01388F

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