CuTC-Catalyzed Ortho -Coupling of Chalcones with Malonates via Cascade Annulation and Transannular Ester Migration: Access to 4-Hydroxy-1,3-dicarboxylatedihydronaphthalenones

We report a CuTC-catalyzed ortho-coupling of ortho-iodochalcones with malonate nucleophiles that proceeds through a cascade reaction accompanied by an unusual transannular ester migration. This transformation establishes a distinct bond-construction sequence that has not previously been applied to ortho-iodochalcone substrates. Under ligand-free and operationally simple conditions, CuTC with Cs₂CO₃ in THF afforded 4-hydroxy-1,3-dicarboxylatedihydronaphthalenones with excellent diastereoselectivity in yields of up to 96%. This method provides direct access to enol-containing tetralin scaffolds with broad potential for synthetic elaboration.