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Type: Journal article
Title: Axially chiral dibenzazepinones by a palladium(0)-catalyzed atropo-enantioselective C−H arylation
Author: Newton, C.
Braconi, E.
Kuziola, J.
Wodrich, M.
Cramer, N.
Citation: Angewandte Chemie International Edition, 2018; 57(34):11040-11044
Publisher: Wiley
Issue Date: 2018
ISSN: 1433-7851
Statement of
Christopher G. Newton, Elena Braconi, Jennifer Kuziola, Dr. Matthew D. Wodrich, Nicolai Cramer
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.
Keywords: C−H activation
asymmetric catalysis
axial chirality
Rights: © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
DOI: 10.1002/anie.201806527
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