Enantioselective Morita-Baylis-Hillman reaction of isatins with acrylates: Facile creation of 3-hydroxy-2-oxindoles

Abstract

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 β-isocupreidine (β-ICD) is believed to facilitate the key proton transfer step in the MBH reaction, via an intramolecular proton relay process. © 2010 American Chemical Society.