Axially Chiral Dibenzazepinones by a Palladium(0)‐Catalyzed Atropo‐enantioselective C−H Arylation |
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| Authors: | Dr. Christopher G. Newton Elena Braconi Jennifer Kuziola Dr. Matthew D. Wodrich Prof. Dr. Nicolai Cramer |
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| Affiliation: | 1. http://isic.epfl.ch/lcsa;2. Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, Lausanne, Switzerland;3. Laboratory for Computational Molecular Design, EPFL SB ISIC LCMD, BCH 5121, Lausanne, Switzerland |
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| Abstract: | Atropo‐enantioselective C?H functionalization reactions are largely limited to the dynamic kinetic resolution of biaryl substrates through the introduction of steric bulk proximal to the axis of chirality. Reported herein is a highly atropo‐enantioselective palladium(0)‐catalyzed methodology that forges the axis of chirality during the C?H functionalization process, enabling the synthesis of axially chiral dibenzazepinones. Computational investigations support experimentally determined racemization barriers, while also indicating C?H functionalization proceeds by an enantio‐determining CMD to yield configurationally stable eight‐membered palladacycles. |
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| Keywords: | asymmetric catalysis atropisomer axial chirality C− H activation palladium |
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