Palladium-Catalyzed Enantioselective Ene and Aldol Reactions with Isatins, Keto Esters, and Diketones: Reliable Approach to Chiral Tertiary Alcohols

Chiral dicationic Pd-complex-catalyzed enantioselective ene and aldol reactions with various isatin derivatives are shown to produce the corresponding 3-hydroxy-2-oxindole products in good yields with high enantioselectivities. These catalytic processes are effective not only with isatins but also with keto esters and diketones derivatives. Even with unprotected isatin, high yields and enantioselectivities were obtained to produce convolutamydine A as a naturally occurring compound. Sequentially, alpha-oxidation by m-CPBA and alpha-fluorination by selectfluor of the ene product could be achieved to give the corresponding alpha-hydroxy and alpha-fluoro ketones, respectively.