Êtes-vous un étudiant de l'EPFL à la recherche d'un projet de semestre?
Travaillez avec nous sur des projets en science des données et en visualisation, et déployez votre projet sous forme d'application sur Graph Search.
An efficient synthesis of functionalized 3-alkyl-3-cyanomethyl-2-oxindole by a palladium-catalyzed domino Heck-cyanation reaction has been developed. Reaction of ortho-iodoanilide with potassium ferro(II)cyanide in the presence of palladium acetate and sodium carbonate afforded oxindole derivs., e.g., I, in good to excellent yields. An enantioselective domino Heck-cyanation process has been developed for the first time using (S)-DIFLUORPHOS as a chiral supporting ligand, and an enantioselectivity of up to 79% ee in the enantiomerically enriched oxindole was obtained under optimized conditions. A concise total synthesis of (+-)-esermethole (II, R = Me) and (+-)-physostigmine (II, R = CONHMe), powerful inhibitors of acetyl- and butyryl-cholinesterase, is also described. [on SciFinder (R)]