Artículo
Thiol-free multicomponent synthesis of non-racemic β-acyloxy thioethers from biocatalytically obtained chiral halohydrins
Fecha de publicación:
12/2023
Editorial:
Royal Society of Chemistry
Revista:
Organic & Biomolecular Chemistry
ISSN:
1477-0520
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A novel multicomponent chemoenzymatic strategy for the preparation of enantioenriched β-acyloxy thioethers has been developed. This robust methodology employs mild bases, air atmosphere, room temperature and avoids the use of foul-smelling thiols. Instead, potassium thioacetate is employed as a universal sulfur source. This chemoselective strategy tolerates aromatic and aliphatic components and diverse functional groups. The chirality is enzymatically defined by ADH-catalyzed bioreduction of α-haloketones delivering an enantioenriched halohydrin which is one of the three components, and the optical purity remains untouched in the final product. Semipreparative scale multicomponent reaction affords high yield of the products (up to 96%).
Palabras clave:
BIOCATALYSIS
,
THIOETHER
,
MCR
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Articulos(CIQUIBIC)
Articulos de CENTRO DE INVEST.EN QCA.BIOL.DE CORDOBA (P)
Articulos de CENTRO DE INVEST.EN QCA.BIOL.DE CORDOBA (P)
Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
López Vidal, Martín Guillermo; Lavandera, Iván; Barra, Jose Luis; Bisogno, Fabricio Román; Thiol-free multicomponent synthesis of non-racemic β-acyloxy thioethers from biocatalytically obtained chiral halohydrins; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 22; 7; 12-2023; 1420-1425
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