Stereoselective Access to β‐gem‐Difluorinated Alcohols Through Enzymatic Reduction

Author:

Bacheley Lucas12,Boutet Julien3,Guillamot Gérard2,Gilles Pierre4,Martin Juliette4,Phansavath Phannarath1,Ratovelomanana‐Vidal Virginie1ORCID

Affiliation:

1. PSL University Chimie ParisTech CNRS UMR 8060 Institute of Chemistry for Life and Health Sciences CSB2D Team 75005 Paris France

2. SEQENS 2-8 rue de Rouen, ZI de Limay-Porcheville 78440 Porcheville France

3. SEQENS 21 chemin de la Sauvegarde 21 Ecully Parc 69130 Ecully France

4. Protéus by SEQENS 70 allée Graham Bell 30035 Nîmes France

Abstract

AbstractWe report here a mild process to access diversely functionalized enantioenriched β‐gem‐difluorinated (S)‐alcohols by using biocatalytic reduction in >99% yield and enantiomeric excesses ranging from 96% to >99%. This novel approach involves enzymatic reduction of α‐gem‐difluorinated heterocyclic and carbocyclic ketone derivatives as well as an acyclic gem‐difluorinated β‐ketosulfone and proceeds under mild conditions at 30 °C under aqueous conditions to produce a range of high added value enantioenriched difluorinated alcohols including 3,3‐difluorochromanol, 3,3‐difluorothiochromanol, 3,3‐difluoro‐dihydroquinolinol, and α‐difluorinated β‐hydroxysulfone derivatives. A comparative study between enzymatic reduction and metal‐catalyzed asymmetric transfer hydrogenation was carried out as well.

Publisher

Wiley

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