Valdez Pérez, L.F., Bachollet, S.P.J.T., Orlov, N.V. et al. (2 more authors) (2023) A dynamic thermodynamic resolution strategy for the stereocontrolled synthesis of streptonigrin. Angewandte Chemie International Edition, 62 (5). 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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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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: | Funder Grant number EUROPEAN COMMISSION - HORIZON 2020 721223 ENGINEERING AND PHYSICAL SCIENCE RESEARCH COUNCIL EP/S018336/1 EUROPEAN COMMISSION - FP6/FP7 ECHONET - 316379 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 17 Nov 2022 12:04 |
Last Modified: | 26 Sep 2024 14:21 |
Status: | Published |
Publisher: | Wiley |
Refereed: | Yes |
Identification Number: | 10.1002/anie.202213692 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:193504 |