| Title | Biocatalytic Atroposelective Synthesis of Axially Chiral N-Arylindoles via Dynamic Kinetic Resolution |
|---|---|
| Authors | Rodriguez-Salamanca, Patricia , de Gonzalo, Gonzalo , CARMONA CARMONA, JOSÉ ALBERTO, Lopez-Serrano, Joaquin , Iglesias-Siguenza, Javier , Fernandez, Rosario , Lassaletta, Jose M. , Hornillos, Valentin |
| External publication | Si |
| Means | ACS Catal. |
| Scope | Article |
| Nature | Científica |
| JCR Quartile | 1 |
| SJR Quartile | 1 |
| JCR Impact | 11.3 |
| SJR Impact | 3.847 |
| Publication date | 06/01/2023 |
| ISI | 000905198600001 |
| DOI | 10.1021/acscatal.2c06175 |
| Abstract | 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. |
| Keywords | asymmetric catalysis; axial chirality; N-aryl indoles; biocatalysis; dynamic kinetic resolution |
| Universidad Loyola members |