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Asymmetric Counteranion-Directed Electrocatalysis for Enantioselective Control of Radical Cation.
Angew Chem Int Ed Engl
January 2025
College of Pharmaceutical Sciences, Zhejiang University of Technology, 310014, Hangzhou, P. R. China.
The control of enantioselectivity in radical cation reactions presents long-standing challenges, despite a few successful examples. We introduce a novel strategy of asymmetric counteranion-directed electrocatalysis to address enantioselectivity in radical cation chemistry. This concept has been successfully demonstrated in two reactions: an asymmetric dehydrogenative indole-phenol [3+2] coupling and an atroposelective C-H/N-H dehydrogenative coupling.
View Article and Find Full Text PDFAtroposelective Silylation of 1,1'-Biaryl-2,6-diols by a Chiral Counteranion Directed Desymmetrization Enhanced by a Subsequent Kinetic Resolution.
Angew Chem Int Ed Engl
July 2023
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.
A desymmetrizing silylation of aromatic diols is reported. The previously unknown asymmetric silyl ether formation of phenol derivatives is achieved by applying List's counteranion directed silylation technique. A silylium-ion-like silicon electrophile generated from an allylic silane paired with an imidodiphosphorimidate (IDPi) enables enantioselective discrimination of achiral 1,1'-biaryl-2,6-diols.
View Article and Find Full Text PDFAsymmetric counteranion-directed photoredox catalysis.
Science
February 2023
Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany.
Photoredox catalysis enables distinctive and broadly applicable chemical reactions, but controlling their selectivity has proven to be difficult. The pursuit of enantioselectivity is a particularly daunting challenge, arguably because of the high energy of the activated radical (ion) intermediates, and previous approaches have invariably required pairing of the photoredox catalytic cycle with an additional activation mode for asymmetric induction. A potential solution for photoredox reactions proceeding via radical ions would be catalytic pairing with enantiopure counterions.
View Article and Find Full Text PDF(SCp)Rhodium-Catalyzed Asymmetric Satoh-Miura Reaction for Building-up Axial Chirality: Counteranion-Directed Switching of Reaction Pathways.
Angew Chem Int Ed Engl
January 2023
Chang-Kung Chuang Institute, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, China.
Satoh-Miura reaction is an important method for extending π-systems by forging multi-substituted benzene rings via double aryl C-H activation and annulation with alkynes. However, the development of highly enantioselective Satoh-Miura reaction remains rather challenging. Herein, we report an asymmetric Satoh-Miura reaction between 1-aryl benzo[h]isoquinolines and internal alkynes enabled by a SCpRh-catalyst.
View Article and Find Full Text PDFChiral Counteranion-Directed Catalytic Asymmetric Methylene Migration Reaction of Ene-Aldimines.
J Org Chem
July 2022
Institute for Molecular Science, Okazaki, Aichi 444-8787, Japan.
A catalytic asymmetric methylene migration reaction of ene-aldimines directed by chiral counteranions is developed, with the optimal catalyst identified as phenanthryl-substituted ()-BINOL phosphate. Control experiments and density functional theory computations reveal the importance of the 2-hydroxy group of the ene-aldimine and attractive (e.g.
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