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Bifunctional Chiral Electrocatalysts Enable Enantioselective α-Alkylation of Aldehydes.
He, Jin-Yu; Zhu, Cuiju; Duan, Wen-Xi; Kong, Ling-Xuan; Wang, Na-Na; Wang, Yan-Zhao; Fan, Zhi-Yong; Qiao, Xin-Ying; Xu, Hao.
Afiliação
  • He JY; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Zhu C; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Duan WX; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Kong LX; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Wang NN; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Wang YZ; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Fan ZY; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Qiao XY; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
  • Xu H; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan, 430079, China.
Angew Chem Int Ed Engl ; 63(39): e202401355, 2024 Sep 23.
Article em En | MEDLINE | ID: mdl-38967087
ABSTRACT
Herein, we describe an innovative approach to the asymmetric electrochemical α-alkylation of aldehydes facilitated by a newly designed bifunctional chiral electrocatalyst. The highly efficient bifunctional chiral electrocatalyst combines a chiral aminocatalyst with a redox mediator. It plays a dual role as a redox mediator for electrooxidation, while simultaneously providing remarkable asymmetric induction for the stereoselective α-alkylation of aldehydes. Additionally, this novel catalyst exhibits enhanced catalytic activity and excellent stereoselective control comparable to conventional catalytic systems. As a result, this strategy provides a new avenue for versatile asymmetric electrochemistry. The electrooxidation of diverse phenols enables the C-H/C-H oxidative α-alkylation of aldehydes in a highly chemo- and stereoselective fashion. Detailed mechanistic studies by control experiments and cyclic voltammetry analysis demonstrate possible reaction pathways and the origin of enantio-induction.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article