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Chiral Phosphine–Silver(I) Complex Catalyzed Enantioselective Interrupted Feist–Bénary Reaction with Ynones: The Aldol–Cycloisomerization Cascade

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journal contribution
posted on 02.07.2015, 00:00 by Debarshi Sinha, Arnab Biswas, Vinod K. Singh
Silver-catalyzed interrupted Feist–Bénary reaction is described for the efficient enantioselective synthesis of dihydrofuran heterocycles. A new method has been developed for the silver­(I)–(R)-BINAP complex mediated aldol–cycloisomerization cascade reaction between ynones and 1,3-diketones to provide functionalized dihydrofurans with moderate to good yields (up to 95%) and good to excellent enantiomeric excess (up to 98%). The presence of an exocyclic double bond and hydroxy group in the dihydrofuran products provides wide scope for further structural manipulation.