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Palladium-Catalyzed [3 + 2] Cycloaddition of Vinylethylene Carbonates with In Situ Generated Ketones from Diazo Compounds and DMSO

  • 0Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, State Key Laboratory of Material-Oriented Chemical Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, China.
The Journal of organic chemistry +

|

June 14, 2025

Abstract

The palladium-catalyzed [3 + 2] cycloaddition of vinylethylene carbonates (VECs) with ketones presents significant challenges with only sporadic examples reported. Herein, we have developed an in situ generation strategy enabling the engagement of polycarbonyl-based ketones in [3 + 2] cycloaddition with VECs. This approach utilizes diazo compounds as latent carbonyl precursors and employs DMSO as both the solvent and oxidant, bypassing issues associated with the isolation of easily hydrated polycarbonyl compounds. By this protocol, various 1,3-dioxolanes bearing two quaternary stereocenters were readily constructed.

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