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.
Bibliographical noteFunding Information:
We acknowledge the EPSRC (DTA award) for funding. We thank Dr. Natalie Pridmore (University of Bristol) for X-ray crystallography analysis and Sayad Doobary (University of Bristol) and Mark Deeprose (University of Bristol) for assistance with conducting cyclic voltammetry experiments.
© 2021 American Chemical Society.