Isatin derivatives are reactive electrophilic components for the Baylis-Hillman reaction

Isatin derivatives readily react as the electrophilic component in the Baylis-Hillman reaction giving good to excellent yields of the respective adducts. It is generally accepted that ketones only take part in the Baylis-Hillman reaction under relatively extreme conditions. with a few exceptions. Isatin on the other hand readily reacts with acrylic acid derivatives in ethanol and or ethanol/THF mixtures in the presence of a catalytic quantity of DABCO. The solid state structures for these novel dioxindole derivatives were determined for two adducts by single-crystal X-ray diffraction spectroscopy, revealing an inside hydroxyl conformation (C) 2002 Elsevier Science Ltd. All rights reserved.