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Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

ABSTRACT: 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.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2536500 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature

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Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

Trost Barry M BM Zhang Yong Y

Journal of the American Chemical Society 20071107 47

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 mec ...[more]

PMID: 17985899

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