Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 47, Pages 14548-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0755717
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Funding
- NIGMS NIH HHS [R01 GM013598-43, R01 GM013598] Funding Source: Medline
- PHS HHS [13598] Funding Source: Medline
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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.
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