Cu<sup>II</sup>/TEMPO‐Catalyzed Enantioselective C(sp<sup>3</sup>)–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation
Pei‐Sen Gao, Xin‐Jun Weng, Zhen‐Hua Wang, Chao Zheng, Bing Sun, Zhihao Chen, Shu‐Li You, Tian‐Sheng Mei
Abstract
Abstract A novel strategy for asymmetric Shono‐type oxidative cross‐coupling has been developed by merging copper catalysis and electrochemistry, affording C1‐alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co‐catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.
Topics & Concepts
IminiumEnantioselective synthesisChemistryOxidizing agentCatalysisElectrochemistryCopperRedoxTetrahydroisoquinolineAlkynylationCombinatorial chemistryOxidative coupling of methaneLigand (biochemistry)Medicinal chemistryOrganic chemistryElectrodeBiochemistryReceptorPhysical chemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions