Enantioselective access to spiro[2,3-dihydrofuran-2,2′-inden-1-ones] via zinc catalyzed [3 + 2] annulation of α-hydroxy-1-indanones with yne–enones

Abstract

The enantioselective [3 + 2] annulation of α-hydroxy-1-indanones with yne–enones was accomplished using dinuclear zinc catalysts via a Brønsted base and Lewis acid cooperative activation model. A wide range of enantioenriched spiro[2,3-dihydrofuran-2,2′-inden-1-one] derivatives were obtained in good yields with excellent diastereoselectivities and enantiostereoselectivities (up to 84% yield, 20 : 1 dr, 99% ee). This transformation features broad substrate scope, gram-scale synthesis, and late-stage functionalization of the complex molecule.