Exploiting Biocatalysis for the Scalable Synthesis of Enantiopure γ‐Hydroxynitrile Building Blocks

Le résumé fourni par la source

We report the scalable biocatalyzed synthesis of γ‐hydroxynitriles from their corresponding prochiral ketone precursors. Screening of a panel of alcohol dehydrogenases (ADHs) identified RRADH as an ( S )‐selective ADH yielding the desired products in e.e. values of 99%, whereas LSADH gave ( R )‐configured γ‐hydroxynitriles (e.e. up to 95%). Optimization of this transformation allowed for reaction scale‐up to 5 mmol, affording the targets in gram quantities. Moreover, the absolute configuration of the ( S )‐configured products was unambiguously established by single‐crystal diffraction. This study showcases how chiral γ‐hydroxynitriles can be generated from readily available γ‐ketonitriles in an efficient and scalable manner, providing a robust and sustainable access to these valuable entities.

Ce résumé expose les affirmations des auteurs. BNTIC ne l’interprète pas comme une validation indépendante des résultats.