Autor según el artículo: Alegre, S. Alberico, E. Pàmies, O. Diéguez, M.

Departamento: Química Física i Inorgànica

Palabras clave: Hydrogenation Enantioselectivity

Resumen: The ligand design of one of the most successful monophosphite ligand classes in Rh-catalyzed hydrogenation was expanded upon by introducing several substituents at the C-3 position of the furanoside backbone. A small but structurally important library of monophosphite ligands was developed by changing the substituents at the C-3 position of the furanoside backbone and the substituents/configurations at the biaryl phosphite group. These new furanoside monophosphite ligands were evaluated in the Rh-catalyzed asymmetric hydrogenation of a,ß-unsaturated carboxylic acid derivatives and enamides. The results show that the effect of introducing a substituent at the C-3 position of the furanoside backbone on the enantioselectivity depends not only on the configuration at the C-3 position of the furanoside backbone and the binaphthyl group but also on the substrate. Thus, the new ligands afforded high to excellent enantioselectivities in the reduction of carboxylic acid derivatives (ee's up to >99.9%) and moderate ee's (up to 67%) in the hydrogenation of enamides.

Áreas temáticas: Chemistry

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

ISSN: 0957-4166

Página final: 262

Volumen de revista: 25

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

Enlace a la fuente original: http://www.sciencedirect.com/science/article/pii/S0957416613005545

DOI del artículo: 10.1016/j.tetasy.2013.12.010

Entidad: Universitat Rovira i Virgili.

Año de publicación de la revista: 2014

Página inicial: 258

Tipo de publicación: Post-print