Palladium-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Michael Acceptors: Construction of Vicinal Quaternary Stereocenters

An efficient method for the diastereo‐ and enantioselective construction of vicinal all‐carbon quaternary stereocenters through palladium‐catalyzed decarboxylative cycloaddition of vinylethylene carbonates with activated Michael acceptors was developed. By using a palladium complex generated in situ from [Pd2(dab)3]⋅CHCl3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process provides multifunctionalized tetrahydrofurans bearing vicinal all‐carbon quaternary stereocenters in high yields with a high level of absolute and relative stereocontrol. Vicinal all‐carbon quaternary stereocenters are constructed through a Pd‐catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates 1 with Michael acceptors 2 (see scheme). By using a palladium complex generated in situ from [Pd2(dab)3]⋅CHCl3 and phosphoramidite L, the process provides multifunctionalized tetrahydrofurans 3 in high yields with high levels of diastereo‐ and enantioselectivities.