Enantioselective Formal C-H Conjugate Addition of Acetanilides to β-Substituted Acrylates by Chiral Iridium Catalysts

Abstract

The Ir-catalyzed enantioselective reaction of substituted acetanilides with β-substituted α,β-unsaturated esters provided chiral 3,3-disubstituted propanoates in high yield with good-to-excellent enantiomeric excess (up to 99 % ee). This transformation, initiated by sp² C-H bond activation, is the first example of enantioselective formal C-H conjugate addition to β-substituted α,β-unsaturated carbonyl compounds. The starting materials are commercially available and/or readily accessible.

Keywords: C−H alkylation; acetanilides; conjugate addition; enantioselective; iridium.