Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate

Abstract

An enantioselective intermolecular carbonyl–ene reaction and a Friedel–Crafts-type reaction of 1,1,2-trisubstituted and 1,2-disubstituted simple olefins with ethyl glyoxylate were developed using F₁₀BINOL-derived N-sulfonyl phosphoramide as the chiral strong Brønsted acid catalyst. The present reactions feature an atom-economical and environmentally benign approach to the synthesis of enantioenriched allylic and homoallylic alcohols.