Valdez Pérez, L.F., Bachollet, S.P.J.T., Orlov, N.V. et al. (2 more authors) (2022) A dynamic thermodynamic resolution strategy for the stereocontrolled synthesis of streptonigrin. Angewandte Chemie International Edition. e202213692. ISSN 1433-7851
Abstract
We report that axially chiral biaryl boronic esters can be generated with control of atropselectivity by a Binol-mediated dynamic thermodynamic resolution process. These intermediates can be progressed to enantioenriched products via stereoretentive functionalization of the carbon-boron bond. Finally, we have exploited this method in the first highly stereoselective total synthesis of P streptonigrin.
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Copyright, Publisher and Additional Information: | © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/4.0/) which permits use, distribution and reproduction in any medium, provided the original work is properly cited. | ||||||||
Keywords: | atropisomers; diastereoselectivity; dynamic thermodynamic resolution; boronic esters; total synthesis | ||||||||
Dates: |
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Institution: | The University of Sheffield | ||||||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||||||
Funding Information: |
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Depositing User: | Symplectic Sheffield | ||||||||
Date Deposited: | 17 Nov 2022 12:04 | ||||||||
Last Modified: | 12 Dec 2022 16:00 | ||||||||
Status: | Published online | ||||||||
Publisher: | Wiley | ||||||||
Refereed: | Yes | ||||||||
Identification Number: | https://doi.org/10.1002/anie.202213692 | ||||||||
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