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

Kohsuke Ohmatsu, Yuichiro Ando, Takashi Ooi*

*Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan, Email: tooiapchem.nagoya-u.ac.jp

K. Ohmatsu, Y. Ando, T. Ooi, Synlett, 2017, 28, 1291-1294.

DOI: 10.1055/s-0036-1558958 (free Supporting Information)


Abstract

Peroxy trichloroacetimidic acid, in situ generated from aqueous hydrogen peroxide and trichloroacetonitrile, acts as a competent electrophilic oxygenating agent for a direct enantioselective α-hydroxylation of oxindoles in the presence of a chiral 1,2,3-triazolium salt as a phase-transfer catalyst.


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Key Words

hydroxylation, carbonyl compound, hydrogen peroxide, imidic acid, oxindoles, chiral ion pair, 1,2,3-triazolium ion, organocatalysis


ID: J60-Y2017