Photoredox Organocatalysis for the Enantioselective Synthesis of 1,7- Dicarbonyl Compounds

Abstract

We describe an asymmetric organocatalytic method to synthesize 1,7-dicarbonyl compounds containing a β-stereocenter. The chemistry relies on the formation of γ-keto radicals, generated upon oxidative ring-opening of cyclobutanols mastered by an organic photoredox catalyst. These non-stabilized primary radicals are stereoselectively intercepted by an iminium ion intermediate, formed upon activation of aliphatic and aromatic enals by a chiral secondary amine catalyst. This organocatalytic photoredox method served to prepare scaffolds found in natural products and drug molecules.