Enantioselective Nucleophilic Vinylic Substitution of Nitroolefins for the Synthesis of 3-Alkenyl Oxindoles

An asymmetric catalytic nucleophilic vinylic substitution (SNV) reaction of 5H-thiazol-4-ones and nitroolefins has been developed for the synthesis of 3-alkenyl oxindoles. The enantioselective SNV reaction with a nitro group as the leaving group proceeded smoothly to afford 3-alkenyl oxindoles in good yields with high regio- and enantioselectivity. The reaction showed broad substrate applicability. A quaternary carbon stereocenter, which was substituted by sp2 carbon, was constructed under mild reaction conditions.