Photoinduced, Palladium-Catalyzed Enantioselective 1,2-Alkylsulfonylation of 1,3-Dienes

Abstract

The chiral allylic sulfonylated group is a unique structural motif embedded in a range of natural products and pharmaceuticals. Notably, the synthesis of structurally diverse chiral allylic sulfonylated derivatives via alkylsulfonylation of 1,3-dienes remains underexplored because of its inherent challenges in stereocontrol and regioselectivity. Herein, photoinduced, palladium-catalyzed enantioselective 1,2-alkylsulfonylation of conjugated 1,3-dienes is described. A wide variety of alkyl bromides, 1,3-dienes, and sodium sulfinates could be facilely coupled to generate value-added chiral allylic sulfonylated derivatives with high enantioselectivity. Finally, the utility of this enantioselective difunctionalization protocol was demonstrated in pharmaceutical analogue synthesis.