American Chemical Society
ja0755717_si_001.cif (17.2 kB)

Mo-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation of 3-Aryloxindoles

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posted on 2007-11-28, 00:00 authored by Barry M. Trost, Yong Zhang
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction mediated by a chiral molybdenum catalyst has been developed as a novel entry into synthetically versatile 3-alkyl-3-aryloxindoles. Extremely bulky nucleophiles were employed to form a quaternary center and an adjacent tertiary center asymmetrically concurrently. The regio- and diastereoselectivity of the reaction is dependent upon the steric and electronic nature of the nucleophiles to an unusual degree. A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed.