A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin.
Luis F Valdez PérezSylvestre P J T BacholletNikolai V OrlovKenji P M KopfJoseph P A HarrityPublished in: Angewandte Chemie (International ed. in English) (2022)
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.