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https://hdl.handle.net/2440/119227
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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 1521-3773 |
Statement of Responsibility: | 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 atropisomer axial chirality palladium |
Rights: | © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
DOI: | 10.1002/anie.201806527 |
Published version: | http://dx.doi.org/10.1002/anie.201806527 |
Appears in Collections: | Aurora harvest 8 Chemistry publications |
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