Quaternary Ammonium (Hypo)iodite Catalysis for Enantioselective Oxidative Cycloetherification

Abstract

Eye for an I Oxidative catalysis is largely the domain of transition metals, whether iron in an enzyme, or rarer palladium in a synthetic system. These metals can efficiently shuttle between oxidation states, easing the transfer of hydrogen and oxygen atoms between hydrocarbons and oxidants. Uyanik et al. (p. 1376 ; see the Perspective by French ) now show that iodine can take the place of the metal to catalytically activate peroxide during the formation of benzofuran derivatives. Pairing iodide anions with chiral ammonium cations allowed the generation of stereoselectivity at levels similar to those seen with metal complexes bearing chiral ligands.