Rodriguez-Salamanca, Patricia , de Gonzalo, Gonzalo , CARMONA CARMONA, JOSÉ ALBERTO, Lopez-Serrano, Joaquin , Iglesias-Siguenza, Javier , Fernandez, Rosario , Lassaletta, Jose M. , Hornillos, Valentin
Si
ACS Catal
Article
Científica
11.3
3.847
06/01/2023
000905198600001
A highly enantioselective biocatalytic dynamic kinetic resolution (DKR) of configurationally labile N-arylindole aldehydes is described. The DKR proceeds by atroposelective bioreduction of the carbonyl group catalyzed by commercial ketoreductases (KREDs), thus affording the corresponding axially chiral N-arylindole aminoalcohols, with excellent conversions and optical purities. The strategy relies on the racemization of the stereogenic axis that takes place thanks to a transient Lewis pair interaction between the NMe2 and the aldehyde groups. This protocol features a broad substrate scope under very mild conditions.
asymmetric catalysis; axial chirality; N-aryl indoles; biocatalysis; dynamic kinetic resolution