Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of -Sulfonyl Cyclopropylamines with Electron-Deficient Olefins.

A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between -sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization.