A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin

Luis F Valdez Pérez; Sylvestre P J T Bachollet; Nikolai V Orlov; Kenji P M Kopf; Joseph P A Harrity

doi:10.1002/anie.202213692

A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin

Angew Chem Int Ed Engl. 2023 Jan 26;62(5):e202213692. doi: 10.1002/anie.202213692. Epub 2022 Dec 7.

Authors

Luis F Valdez Pérez¹, Sylvestre P J T Bachollet¹, Nikolai V Orlov¹, Kenji P M Kopf¹, Joseph P A Harrity¹

Affiliation

¹ Department of Chemistry, The University of Sheffield, Sheffield, S3 7HF, UK.

Abstract

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.

Keywords: Atropisomers; Boronic Esters; Diastereoselectivity; Dynamic Thermodynamic Resolution; Total Synthesis.

Abstract

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