A Sequential Transition Metal and Organocatalytic Approach to the Enantioselective Synthesis of C2-Spiroindoline Systems

We report herein an organocatalyzed enantioselective spirocyclization strategy to access valuable C2-spiroindoline scaffolds bearing a quaternary stereocenter via an aza-Michael addition reaction, wherein the acid additive plays the role of dual functionality. The substrates for this key step were put together by an exo-selective, Pd-catalyzed γ-arylation of silyldienol ethers of the corresponding cyclohexenones. A close alliance between a low catalyst loading and a slow reaction rate yields C2-spiroindolines with good enantioselectivity.