Late-Stage Chemo- and Enantioselective Oxidation of Indoles to C3-Monosubstituted Oxindoles.
Late-Stage Chemo- and Enantioselective Oxidation of Indoles to C3-Monosubstituted Oxindoles.
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DOI：
10.1021/jacs.3c11742
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发表时间：
2023-12
影响因子：
15
通讯作者：
Song Li;Xigong Liu;C. Tung;Lei Liu
中科院分区：
文献类型：
--
作者：
Song Li;Xigong Liu;C. Tung;Lei Liu
Catalytic asymmetric preparation of chiral 3-monosubstituted oxindoles represents a significant challenge in synthetic chemistry due to the ease of racemization of the tertiary stereocenter through enolization. Here, we describe a general titanium-catalyzed chemo- and enantioselective indole oxidation to produce a diverse set of chiral 3-monosubstituted oxindoles with up to 96% yield, 99% ee, and with a substrate/catalyst ratio of 10,000 by using the combination of a simple titanium(salan) catalyst with green and atom-economic terminal oxidant H2O2. The mild approach tolerates a broad range of functional groups, enabling late-stage asymmetric diversification of a series of commercial drugs and natural products together with late-stage asymmetric construction of a wide set of enzyme antagonists, all of which are difficult to achieve through existing methods.
