Enantioselective Morita-Baylis-Hillman Reaction of Isatins with Acrylates: Facile Creation of 3-Hydroxy-2-oxindoles

The first tertiary amine catalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins with acrylates has been demonstrated, allowing asymmetric synthesis of biologically significant 3-substituted-3-hydroxy-2-oxindoles in good yields and with excellent enantioselectivities. The C6'-OH group of beta-isocupreidine (beta-ICD) is believed to facilitate the key proton transfer step in the MBH reaction, via an intramolecular proton relay process.