Construction of chiral 3-alkenyl-3-substituted oxindoles by stereoselective direct alkenylation of isatin derivatives and 3-vinylindoles

An efficient asymmetric alkenylation between 3-vinylindoles and isatin derivatives was developed under catalysis of a chiral copper complex. A series of optically active 3-alkenyl-3-substituted oxindoles were obtained in excellent yields and stereoselectivities. The reaction mechanism was proposed and supported by DFT calculation. [Display omitted] we developed an alkenylation reaction of isatin derivatives and 3-vinylindoles. A series of chiral 3-alkenyl-3-substituted oxindole derivatives were obtained with excellent yields (up to 99%) and stereoselectivities (up to 99% ee, >20:1 dr). Scaling up the reaction to gram quantities, the desired product 4b could be obtained with a good yield (88%) and a great ee value (87%, >20:1 dr). Also, the reaction transition state with a π-π interaction was proposed, which was supported by DFT calculations. Notably, the products are rich in functional group conversion and have great potential application for the synthesis of some natural products and drug molecules.