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

A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N- 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. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.

Automated summary

The reaction described is a highly diastereoselective visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins, leading to the construction of trans-cyclopentanes with synthetically useful functional groups. This reaction proceeds via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical and subsequent 5-exo cyclization.