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Article Abstract
A novel series of spiro[benzofuran-2,5'-isoxazolidine] compounds was successfully synthesized using a catalyst-free 1,3-DC reaction between benzofuran-derived azadienes (BDAs) and nitrones. This methodology achieved high regio- and diastereoselectivity and demonstrated remarkable tolerance toward various functional groups in both BDAs and nitrones, yielding products with good to excellent efficiencies (79-99%). Gram-scale synthesis and subsequent functional transformations further validated the application value of this method for further functionalization.
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Highly Regio- and Diastereoselective 1,3-DC Reaction of BDAs and Nitrones: Synthesis of the Spiro[benzofuran-2,5'-isoxazolidine] Framework.
J Org Chem
June 2025
Pingyuan Laboratory, Key Laboratory of Antiviral Drugs, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
A novel series of spiro[benzofuran-2,5'-isoxazolidine] compounds was successfully synthesized using a catalyst-free 1,3-DC reaction between benzofuran-derived azadienes (BDAs) and nitrones. This methodology achieved high regio- and diastereoselectivity and demonstrated remarkable tolerance toward various functional groups in both BDAs and nitrones, yielding products with good to excellent efficiencies (79-99%). Gram-scale synthesis and subsequent functional transformations further validated the application value of this method for further functionalization.
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