Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 3, Pages 961-967Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200601016
Keywords
alkaloids; asymmetric synthesis; cyanation; domino reactions; oxindoles
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An efficient synthesis of functionalized 3-alkyl-3-cyanomethyl-2-oxindole 1 by a palladium-catalyzed domino Heck-cyanation reaction has been developed. Reaction of ortho-iodoanilide 5 with potassium ferro(II)cyanide, K-4[Fe(CN)(6)], dissolved in DMF in the presence of palladium acetate and sodium carbonate afforded oxindole 1 in good to excellent yields. An enantioselective domino Heck-cyanation process has been developed for the first time using (S)-DIFLUOR-PHOS 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 esermetbole and physostigmine, powerful inhibitors of acetyl- and butyryl-cholinesterase, is documented.
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