posted on 2022-12-22, 18:36authored byPatricia Rodríguez-Salamanca, Gonzalo de Gonzalo, José A. Carmona, Joaquín López-Serrano, Javier Iglesias-Sigüenza, Rosario Fernández, José M. Lassaletta, Valentín Hornillos
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.