Electrochemical Reductive Bimolecular Cycloaddition of 2-Arylideneindane-1,3-diones for the Synthesis of Spirocyclopentanole Indane-1,3-diones

Abstract

An electrochemical reductive bimolecular cycloaddition of 2-arylideneindane-1,3-diones has been reported for the synthesis of spirocyclopentanole indane-1,3-diones bearing five contiguous stereocenters with vicinal tetrasubstituted stereocenters, especially involving a quaternary carbon center, in moderate to good yields and excellent diastereoselectivities. The present protocol features mild reaction conditions, no external chemical redox reagents, excellent atom economy, and gram-scale synthesis. In addition, a mechanistic investigation indicates that the reactions proceed through a radical pathway.