Extended Version of the Corey–Chaykovsky Reaction: Synthesis of 2,4-Substituted Furans by the Treatment of β‑Dialkylamino Chalcones with Dimethylsulfonium Methylide

We describe the synthesis of functionalized furans using the concept of the extended Corey–Chaykovsky reaction. Namely, β,β-disubstituted α,β-unsaturated ketones were treated with dimethylsulfonium methylide to give vinyloxiranes, which immediately rearranged into the corresponding furans. The devel...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-07, Vol.88 (13), p.8227-8235
Main Authors: Shcherbakov, Roman O., Myasnikov, Danil A., Trushkov, Igor V., Uchuskin, Maxim G.
Format: Article
Language:English
Subjects:
Furans
Ketones
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Summary:We describe the synthesis of functionalized furans using the concept of the extended Corey–Chaykovsky reaction. Namely, β,β-disubstituted α,β-unsaturated ketones were treated with dimethylsulfonium methylide to give vinyloxiranes, which immediately rearranged into the corresponding furans. The developed approach allows for synthesizing a broad range of unsymmetrically di- and trisubstituted furans containing various functionalities in the core.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00203