Article
Biocatalytic Atroposelective Synthesis of Axially Chiral N-Arylindoles via Dynamic Kinetic Resolution
Author/s | Rodríguez Salamanca, Patricia
Gonzalo Calvo, Gonzalo de Carmona, José A. López Serrano, Joaquín Iglesias Sigüenza, Francisco Javier Fernández Fernández, Rosario Fátima Lassaletta, José M. Hornillos, Valentín |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2022-12-22 |
Deposit Date | 2024-02-06 |
Published in |
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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 ... 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. |
Funding agencies | Ministerio de Ciencia e Innovación (MICIN). España European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) Junta de Andalucía |
Project ID. | PID2019-106358GB-C21
PID2019-106358GB-C22 P18-FR-3531 P18-FR-644 US-1262867 US-1260906 |
Citation | Rodríguez Salamanca, P., Gonzalo Calvo, G.d., Carmona, J.A., López Serrano, J., Iglesias Sigüenza, F.J., Fernández Fernández, R.F.,...,Hornillos, V. (2022). Biocatalytic Atroposelective Synthesis of Axially Chiral N-Arylindoles via Dynamic Kinetic Resolution. ACS Catalysis, 13 (1), 659-664. https://doi.org/10.1021/acscatal.2c06175. |
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