Mo-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation of 3-Aryloxindoles
- 7 November 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (47), 14548-14549
- https://doi.org/10.1021/ja0755717
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.Keywords
This publication has 20 references indexed in Scilit:
- Regioselective and Enantioselective Iridium-Catalyzed Allylation of EnaminesJournal of the American Chemical Society, 2007
- Molybdenum-Catalyzed Asymmetric Allylation of 3-Alkyloxindoles: Application to the Formal Total Synthesis of (−)-PhysostigmineJournal of the American Chemical Society, 2006
- Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Cu-Catalyzed Conjugate Addition of Dialkylzinc Reagents to 5-(1-Arylalkylidene) Meldrum's AcidsJournal of the American Chemical Society, 2006
- Palladium‐Catalyzed Asymmetric Allylation of Prochiral Nucleophiles: Synthesis of 3‐Allyl‐3‐Aryl OxindolesAngewandte Chemie International Edition, 2004
- 5H-Oxazol-4-ones as Building Blocks for Asymmetric Synthesis of α-Hydroxycarboxylic Acid DerivativesJournal of the American Chemical Society, 2004
- Conclusive Evidence for a Retention−Retention Pathway for the Molybdenum-Catalyzed Asymmetric AlkylationJournal of the American Chemical Society, 2003
- Reactivity of [MCl(η3-allyl)(1,10-phenanthroline)(CO)2] (M = Mo, W) Complexes toward Enolate AnionsOrganometallics, 2003
- Synthesis and Aldol Reactivity of O- and C-Enolate Complexes of NickelJournal of the American Chemical Society, 2003
- Asymmetric Molybdenum-Catalyzed AlkylationsJournal of the American Chemical Society, 1998
- Synthesis of ruthenium enolate (PMe3)4Ru(Me)(OC(CH2)Me) as an equilibrium mixture of oxygen- and carbon-bound transition-metal enolates. Thermal elimination of methane to form an .eta.4-oxatrimethylenemethane complexJournal of the American Chemical Society, 1990