Author, as appears in the article.: Coll, M. Pàmies, O. Diéguez, M.
Department: Química Física i Inorgànica
Keywords: Hydrogenation
Abstract: 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.
Thematic Areas: Catalysis
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 1615-4150
Last page: 2302
Journal volume: 356
Papper version: info:eu-repo/semantics/acceptedVersion
Link to the original source: http://onlinelibrary.wiley.com/doi/10.1002/adsc.201301112/abstract
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Article's DOI: 10.1002/adsc.201301112
Entity: Universitat Rovira i Virgili.
Journal publication year: 2014
First page: 2293
Repositori URV