Atroposelective Synthesis of 2-(Quinolin-8-yl)benzyl Alcohols by Biocatalytic Dynamic Kinetic Resolutions

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...

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Detalles Bibliográficos
Autores: 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.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/160538
Acceso en línea:https://hdl.handle.net/11441/160538
https://doi.org/10.1002/adsc.202301310
Access Level:acceso abierto
Palabra clave:Axial chirality
Asymmetric catalysis
Ketoreductases
Dynamic kinetic resolution
Quinolines
Descripción
Sumario: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.

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