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Cobaltaelectro‐Catalyzed C–H Activation for Central and Axial Double Enantio‐Induction

Tristan von Münchow, Yi‐Ru Liu, Rahul Parmar, Sven Erik Peters, Sven Trienes, Lutz Ackermann

2024Angewandte Chemie International Edition49 citationsDOIOpen Access PDF

Abstract

In recent years, enantioselective electrocatalysis has surfaced as an increasingly-effective platform for sustainable molecular synthesis. Despite indisputable progress, strategies that allow the control of two distinct stereogenic elements with high selectivity remain elusive. In contrast, we, herein, describe electrochemical cobalt-catalyzed C-H activations that enable the installation of chiral stereogenic centers along with a chiral axis with high levels of enantio- and diastereoselectivities. The developed electrocatalysis strategy allowed for C-H/N-H activations/annulations with cyclic and non-cyclic alkenes providing expedient access to various central as well as atropo-chiral dihydroisoquinolinones paired to the valuable hydrogen evolution reaction. Studies on the atropo-stability of the obtained compounds demonstrated that the exceedingly mild conditions ensured by the electrocatalytic process were key for the achieved high stereoselectivities.

Topics & Concepts

StereocenterElectrocatalystCatalysisEnantioselective synthesisElectrochemistrySelectivityChemistryCombinatorial chemistryCobaltNanotechnologyStereochemistryMaterials scienceOrganic chemistryElectrodePhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
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