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Título : One-pot two-step chemoenzymatic deracemization of allylic alcohols using laccases and alcohol dehydrogenases
Autor : Albarrán Velo, Jesús
Lavandera, Iván
Gotor Fernández, Vicente
Palabras clave : Química
Fecha de publicación : 7-jul-2020
Editorial : Elsevier
Citación : Mol. Catal. 2020, 493, 111087
Resumen : A series of enantioenriched (hetero)aromatic secondary allylic alcohols has been synthesized through deracemization of the corresponding racemic mixtures combining a non-selective chemoenzymatic oxidation (laccase from Trametes versicolor and oxy-radical TEMPO) and a stereoselective biocatalyzed reduction (lyophilized cells of E. coli overexpressing an alcohol dehydrogenase, ADH). Both steps were performed in aqueous medium under very mild reaction conditions. After optimization, a sequential one-pot two-step protocol was set up, obtaining the corresponding chiral alcohols in moderate to high conversions (48-95%) and enantiomeric excess (65->99% ee). Depending on the ADH stereopreference, both antipodes from these valuable chiral synthons could be prepared, even at preparative scale (119-178 mg), in a straightforward manner.
URI : http://ria.asturias.es/RIA/handle/123456789/14045
Aparece en las colecciones: Química

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