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
Descripción
Sumario: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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