Author, as appears in the article.: Margalef J, Pàmies O, Diéguez M

Department: Química Física i Inorgànica Química Física i Inorgànica

e-ISSN: 1521-3765

URV's Author/s: Diéguez Fernández, Montserrat / Pamies Ollé, Oscar

Keywords: Rhodium Phosphite-thioether ligands Iridium Cyclic ¿-enamides Cyclic ?-enamides Asymmetric hydrogenation phosphite-thioether ligands iridium cyclic ?-enamides asymmetric hydrogenation

Abstract: Phosphite-thioether ligands with a simple modular architecture, derived from inexpensive l-(+)-tartaric acid and d-mannitol, have been for the first time successfully applied (ee values up to 99 %) in the synthesis of 2-aminotetralines and 3-aminochromanes by metal-catalyzed asymmetric hydrogenation of cyclic ¿-enamides. The ligands have the advantages of the robustness of the thioether/phosphite moieties and the extra control provided by the flexibility of the chiral pocket through the presence of a biaryl phosphite group and a modular carbohydrate-derived backbone. Moreover, they are solid and stable to air and they are therefore easy to handle, manipulate, and store. Usefully, both enantiomers of the hydrogenated products were obtained by simply switching from Rh to Ir. Low hydrogen pressure and environmentally friendly propylene carbonate can be used, with no loss of selectivity.

Research group: Organometàl·lics i Catàlisi Homogènia

Thematic Areas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física

ISSN: 15213765

Author's mail: montserrat.dieguez@urv.cat oscar.pamies@urv.cat

Author identifier: 0000-0002-8450-0656 0000-0002-2352-8508

Last page: 822

Record's date: 2023-07-31

Journal volume: 23

Papper version: info:eu-repo/semantics/acceptedVersion

Link to the original source: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201604483

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Chemistry-A European Journal. 23 (4): 813-822

APA: Margalef J, Pàmies O, Diéguez M (2017). Phosphite-Thiother Ligands Derived from Carbohydrates allow the Enantioswitchable Hydrogenation of Cyclic ¿-Enamides by using either Rh or Ir Catalysts. Chemistry-A European Journal, 23(4), 813-822. DOI: 10.1002/chem.201604483

Article's DOI: 10.1002/chem.201604483

Entity: Universitat Rovira i Virgili

Journal publication year: 2017

First page: 813

Publication Type: Journal Publications