Journal
SYNLETT
Volume 28, Issue 11, Pages 1291-1294Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1558958
Keywords
hydroxylation; carbonyl compound; hydrogen peroxide; imidic acid; oxindole; chiral ion pair; 1,2,3-triazolium ion
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Funding
- CREST (JST)
- JSPS KAKENHI [JP16H01015]
- Program for Leading Graduate Schools 'Integrative Graduate Education and Research Program in Green Natural Sciences' at Nagoya University
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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 alpha-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 alpha-hydroxycarbonyl compounds.
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