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光氧化还原不对称催化 3-氯吲哚的取代反应。

Photoredox asymmetric catalytic enantioconvergent substitution of 3-chlorooxindoles.

机构信息

Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, P. R. China.

出版信息

Chem Commun (Camb). 2019 Sep 19;55(76):11362-11365. doi: 10.1039/c9cc05304b.

Abstract

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.

摘要

报告了在可见光照射下,3-取代 3-氯氧吲哚与 N-芳基甘氨酸的对映选择性取代反应。一种无过渡金属的协同催化平台,以二氰基吡嗪衍生的发色团(DPZ)作为光氧化还原催化剂和手性 Brønsted 酸催化剂,对于这些转化是有效的,其中涉及单电子转移氧化还原步骤和对映选择性自由基偶联。各种有价值的手性 3-亚氨基-3-取代氧吲哚可以以高产率和对映选择性直接合成。

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