Synergistic Catalysis: Highly Enantioselective Cascade Reaction for the Synthesis of Dihydroacridines

Abstract

The first stereoselective synthesis of dihydroacridines through synergistic catalysis, achieving the final target compounds with good to excellent yields and good to excellent enantioselectivities and diastereoselectivities, is reported. The synergistic approach consists in the activation of substituted quinolines with a Lewis acid catalyst that react in a cascade fashion with activated enals in the iminium form. Mechanistic calculations support a consecutive Michael-aldol reaction, followed by dehydration.

Keywords: acridine; diastereoselective; enantioselective; synergistic catalysis; ytterbium.