Copper-Catalyzed Regioselective Annulation of β-Keto Esters and Propargyl Acetates: Access to Polysubstituted Furans

A copper-catalyzed regioselective annulation reaction, conducted without ligands or oxidants, has been developed for the preparation of multisubstituted furans from the readily available starting materials, β-keto esters and propargyl acetates. This process accommodates a wide range of functional groups, resulting in furan skeletons with diverse substitution patterns. The method's potential synthetic utility is highlighted by its applicability in gram-scale preparations and late-stage modifications of natural products.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-20
DOI
https://doi.org/10.1021/acs.joc.4c02408
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Copper-Catalyzed Regioselective Annulation of β-Keto Esters and Propargyl Acetates: Access to Polysubstituted Furans

Yuzhu Yang, Fei Li, Hongke Xu, Yuchen Yang
The Journal of Organic Chemistry
Catalytic Alkyne Reactions
article

Copper-Catalyzed Regioselective Annulation of β-Keto Esters and Propargyl Acetates: Access to Polysubstituted Furans

Yuzhu Yang, Fei Li, Hongke Xu, Yuchen Yang
article en

Abstract

A copper-catalyzed regioselective annulation reaction, conducted without ligands or oxidants, has been developed for the preparation of multisubstituted furans from the readily available starting materials, β-keto esters and propargyl acetates. This process accommodates a wide range of functional groups, resulting in furan skeletons with diverse substitution patterns. The method's potential synthetic utility is highlighted by its applicability in gram-scale preparations and late-stage modifications of natural products.

The Journal of Organic ChemistryVol. 90(1)
Guiyang Medical University (CN), Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences (CN)
West Light Foundation of the Chinese Academy of Sciences, State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University
Openalex Percentile: Top 83%
Catalytic Alkyne Reactions
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