A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin

We report that axially chiral biaryl boronic esters can be generated with control of atroposelectivity by a Binol‐mediated dynamic thermodynamic resolution process. These intermediates can be progressed to enantioenriched products through stereoretentive functionalization of the carbon–boron bond. F...

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Detalles Bibliográficos
Autores principales: Valdez Pérez, Luis F., Bachollet, Sylvestre P. J. T., Orlov, Nikolai V., Kopf, Kenji P. M., Harrity, Joseph P. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107650/
https://www.ncbi.nlm.nih.gov/pubmed/36377668
http://dx.doi.org/10.1002/anie.202213692
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author Valdez Pérez, Luis F.
Bachollet, Sylvestre P. J. T.
Orlov, Nikolai V.
Kopf, Kenji P. M.
Harrity, Joseph P. A.
author_facet Valdez Pérez, Luis F.
Bachollet, Sylvestre P. J. T.
Orlov, Nikolai V.
Kopf, Kenji P. M.
Harrity, Joseph P. A.
author_sort Valdez Pérez, Luis F.
collection PubMed
description We report that axially chiral biaryl boronic esters can be generated with control of atroposelectivity by a Binol‐mediated dynamic thermodynamic resolution process. These intermediates can be progressed to enantioenriched products through 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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spelling pubmed-101076502023-04-18 A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin Valdez Pérez, Luis F. Bachollet, Sylvestre P. J. T. Orlov, Nikolai V. Kopf, Kenji P. M. Harrity, Joseph P. A. Angew Chem Int Ed Engl Communications We report that axially chiral biaryl boronic esters can be generated with control of atroposelectivity by a Binol‐mediated dynamic thermodynamic resolution process. These intermediates can be progressed to enantioenriched products through stereoretentive functionalization of the carbon–boron bond. Finally, we have exploited this method in the first highly stereoselective total synthesis of P‐streptonigrin. John Wiley and Sons Inc. 2022-12-07 2023-01-26 /pmc/articles/PMC10107650/ /pubmed/36377668 http://dx.doi.org/10.1002/anie.202213692 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Valdez Pérez, Luis F.
Bachollet, Sylvestre P. J. T.
Orlov, Nikolai V.
Kopf, Kenji P. M.
Harrity, Joseph P. A.
A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
title A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
title_full A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
title_fullStr A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
title_full_unstemmed A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
title_short A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
title_sort dynamic thermodynamic resolution strategy for the stereocontrolled synthesis of streptonigrin
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107650/
https://www.ncbi.nlm.nih.gov/pubmed/36377668
http://dx.doi.org/10.1002/anie.202213692
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