In Situ Electrophilic Activation of Hydrogen Peroxide for Catalytic Asymmetric α-Hydroxylation of 3-Substituted Oxindoles

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  • Takashi Ooi
    Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering
  • Kohsuke Ohmatsu
    Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering
  • Yuichiro Ando
    Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering

Bibliographic Information

Published
2017-02-27
Resource Type
journal article
DOI
  • 10.1055/s-0036-1558958
Publisher
Georg Thieme Verlag KG

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Description

<jats:p>Peroxy trichloroacetimidic acid, in situ generated from aqueous hydrogen peroxide and trichloroacetonitrile, was found to act as a competent electrophilic oxygenating agent for the direct α-hydroxylation of oxindoles. The use of chiral 1,2,3-triazolium salt as a phase-transfer catalyst enabled rigorous absolute stereocontrol in the carbon–oxygen bond-forming reaction. The present study provides a new, yet practical method for straightforward access to optically active α-hydroxycarbonyl compounds.</jats:p>

Journal

  • Synlett

    Synlett 28 (11), 1291-1294, 2017-02-27

    Georg Thieme Verlag KG

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