Artículo
Atroposelective Synthesis of 2-(Quinolin-8-yl)benzyl Alcohols by Biocatalytic Dynamic Kinetic Resolutions
Autor/es | Coto Cid, Juan Manuel
Gonzalo Calvo, Gonzalo de Carmona, José A. Iglesias Sigüenza, Francisco Javier Rodríguez Salamanca, Patricia Fernández Fernández, Rosario Fátima Hornillos, Valentín Lassaletta, José M. |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2023-12-22 |
Fecha de depósito | 2024-06-14 |
Publicado en |
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Resumen | A highly enantioselective biocatalytic dynamic kinetic resolution (DKR) of 2-(quinoline-8-yl) 3-methylbenzaldehydes and 1-naphthaldehydes is described. The reaction proceeds by atroposelective carbonyl reduction catalyzed ... A highly enantioselective biocatalytic dynamic kinetic resolution (DKR) of 2-(quinoline-8-yl) 3-methylbenzaldehydes and 1-naphthaldehydes is described. The reaction proceeds by atroposelective carbonyl reduction catalyzed by commercial ketoreductases (KREDs), generally reaching high conversions and excellent enantiomeric excesses. Both atropoisomers of the final alcohols can be obtained by a proper selection of the biocatalyst. The DKR strategy relies in the racemization of the stereogenic axis that takes place thanks to a transient Lewis acid-base interaction (LABI) between the nitrogen in the quinoline and the carbonyl group. |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) Junta de Andalucía |
Identificador del proyecto | PID2019-106358GB−C21
PID2019-106358GB−C22 P18-FR-3531 P18-FR-644 US-1262867 US-1260906 |
Cita | Coto Cid, J.M., Gonzalo Calvo, G.d., Carmona, J.A., Iglesias Sigüenza, F.J., Rodríguez Salamanca, P., Fernández Fernández, R.F.,...,Lassaletta, J.M. (2023). Atroposelective Synthesis of 2-(Quinolin-8-yl)benzyl Alcohols by Biocatalytic Dynamic Kinetic Resolutions. Advanced Synthesis & Catalysis, 366 (4), 909-915. https://doi.org/10.1002/adsc.202301310. |
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