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Tandem Photoredox-Chiral Phosphoric Acid Catalyzed Radical–Radical Cross-Coupling for Enantioselective Synthesis of 3-Hydroxyoxindoles
Organic Letters ( IF 5.2 ) Pub Date : 2021-08-30 , DOI: 10.1021/acs.orglett.1c02510
Yang Zhang 1 , Dan Ye 1 , Lei Shen 1 , Kangjiang Liang 1 , Chengfeng Xia 1
Affiliation  

A photochemical protocol that couples diarylamines and α-ketoesters to afford the chiral 3-hydroxyoxindoles through tandem photoredox and chiral phosphoric acid catalysis is developed. The reaction involves an enantioselective photochemical radical–radical cross-coupling process. The chiral phosphoric acid is discovered to play crucial roles by decreasing the reductive potentials of α-ketoesters and stereocontrolling the downstream asymmetric radical–radical cross-coupling via the formation of pentacoordinate complex.

中文翻译:

串联光氧化还原-手性磷酸催化自由基-自由基交叉偶联用于对映选择性合成 3-羟基吲哚

开发了一种光化学方案,通过串联光氧化还原和手性磷酸催化将二芳基胺和 α-酮酯偶联以提供手性 3-羟基吲哚。该反应涉及对映选择性光化学自由基 - 自由基交叉偶联过程。发现手性磷酸通过降低 α-酮酯的还原电位和通过形成五配位络合物来立体控制下游不对称自由基 - 自由基交叉偶联而发挥关键作用。
更新日期:2021-09-17
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