Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library: Scope and limitations

Alegre, S. Alberico, E. Pàmies, O. Diéguez, M.

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Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library: Scope and limitations - PC:686

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https://hdl.handle.net/20.500.11797/PC686

Author, as appears in the article.:	Alegre, S. Alberico, E. Pàmies, O. Diéguez, M.
Journal publication year:	2014
Publication Type:	Post-print
ISSN:	0957-4166
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.
Article's DOI:	10.1016/j.tetasy.2013.12.010
Link to the original source:	http://www.sciencedirect.com/science/article/pii/S0957416613005545
Papper version:	info:eu-repo/semantics/submittedVersion
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:	Chemistry
Keywords:	Hydrogenation Enantioselectivity
Entity:	Universitat Rovira i Virgili.
First page:	258
Last page:	262
Journal volume:	25

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Description:	10.1016/j.tetasy.2013.12.010 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.
Coverage:	Anglès
Type:	Post-print Post-print info:eu-repo/semantics/submittedVersion
Contributor:	Química Física i Inorgànica Universitat Rovira i Virgili.
Títol:	Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library: Scope and limitations
Subject:	Hydrogenation Enantioselectivity Chemistry 0957-4166
Date:	2014
Creator:	Alegre, S. Alberico, E. Pàmies, O. Diéguez, M.
Rights:	info:eu-repo/semantics/openAccess

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