Autor según el artículo: Coll, M. Pàmies, O. Diéguez, M.

Departamento: Química Física i Inorgànica

Palabras clave: Hydrogenation

Resumen: A large library of pyranoside‐based hydroxyamide and thioamide ligands has been synthesized for asymmetric transfer hydrogenation in an attempt to expand the scope of the substrates to cover a broader range of challenging heteroaromatic and aryl/fluoroalkyl ketones. These ligands have the advantage that they are prepared from commercial D‐glucose, D‐glucosamine and α‐amino acids, inexpensive natural chiral feedstocks. By carefully selecting the ligand components (substituents/configurations at the amide/thioamide moiety, the position of amide/thioamide group and the configuration at C‐2), we found that pyranoside‐based thioamide ligands provided excellent enantioselectivities (in the best cases, ees of >99% were achieved) in a broad range of ketones, including the less studied heteroaromatics and challenging aryl/fluoroalkyls. Note that both enantiomers of the reduction products can be obtained with excellent enantioselectivities by simply changing the absolute configuration of the thioamide substituent.

Áreas temáticas: Catalysis

Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 1615-4150

Página final: 2302

Volumen de revista: 356

Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion

Enlace a la fuente original: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201301112/abstract

DOI del artículo: 10.1002/adsc.201301112

Entidad: Universitat Rovira i Virgili.

Año de publicación de la revista: 2014

Página inicial: 2293