Photoredox asymmetric catalytic enantioconvergent substitution of 3-chlorooxindoles

An enantioconvergent substitution of 3-substituted 3-chlorooxindoles with N -aryl glycines under visible light irradiation is reported. A transition-metal-free cooperative catalysis platform with a dicyanopyrazine-derived chromophore (DPZ) as a photoredox catalyst and a chiral Brønsted acid catalyst...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019, Vol.55 (76), p.11362-11365
Hauptverfasser: Zeng, Guangkuo, Li, Yunqiang, Qiao, Baokun, Zhao, Xiaowei, Jiang, Zhiyong
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Sprache:eng
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Zusammenfassung:An enantioconvergent substitution of 3-substituted 3-chlorooxindoles with N -aryl glycines under visible light irradiation is reported. A transition-metal-free cooperative catalysis platform with a dicyanopyrazine-derived chromophore (DPZ) as a photoredox catalyst and a chiral Brønsted acid catalyst is effective for these transformations, which involve a single-electron transfer redox step and an enantioselective radical coupling. A variety of valuable chiral 3-aminomethylene-3-substituted oxindoles can be directly synthesized with high yields and enantioselectivities. An enantioconvergent substitution of 3-substituted 3-chlorooxindoles with N -aryl glycines under visible light irradiation is reported.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc05304b