期刊
SYNLETT
卷 28, 期 11, 页码 1291-1294出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1558958
关键词
hydroxylation; carbonyl compound; hydrogen peroxide; imidic acid; oxindole; chiral ion pair; 1,2,3-triazolium ion
资金
- CREST (JST)
- JSPS KAKENHI [JP16H01015]
- Program for Leading Graduate Schools 'Integrative Graduate Education and Research Program in Green Natural Sciences' at Nagoya University
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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