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