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 developed approach allows for synthesizing a broad range of unsymmetrically di- and trisubstituted furans containing various functionalities in the core.