Author, as appears in the article.: Alegre, S. Alberico, E. Pàmies, O. Diéguez, M.
Department: Química Física i Inorgànica
Keywords: Hydrogenation Enantioselectivity
Abstract: 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.
Thematic Areas: Chemistry
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 0957-4166
Last page: 262
Journal volume: 25
Papper version: info:eu-repo/semantics/submittedVersion
Link to the original source: http://www.sciencedirect.com/science/article/pii/S0957416613005545
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Article's DOI: 10.1016/j.tetasy.2013.12.010
Entity: Universitat Rovira i Virgili.
Journal publication year: 2014
First page: 258
Publication Type: Post-print
Repositori URV