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New sulfur-phosphine ligands derived from sugars: synthesis and application in palladium-catalyzed allylic alkylation and in rhodium asymmetric hydrogenation

 

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Opened Access New sulfur-phosphine ligands derived from sugars: synthesis and application in palladium-catalyzed allylic alkylation and in rhodium asymmetric hydrogenation
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Author: Khiar, Noureddine
Navas, Raquel
Álvarez González, Eleuterio
Fernández Fernández, Inmaculada
Department: Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica
Date: 2008
Published in: Arkivoc, 2008 (8), 211-224.
Document type: Article
Abstract: An efficient route to mixed phosphine / thioglycoside ligands type IV starting from glucose pentaacetate is reported. In only five steps the key epoxide 6 has been obtained in high yield and its structure determined by X-ray analysis. The ring opening of the tert-butyl 4,6-O-benzylidene- 2,3-anhydro-1-thio-β-D-allopyranoside 6 with diphenylphosphinyl lithium afforded the desired ligand as a single diastereoisomer. The prepared compounds act as a bidentate ligands as shown by X-ray analysis of the Rh(I)-complex 12. Preliminary results on the behaviour of these ligands in Pd(0)-catalyzed allylic alkylation, and in Rh(I)-catalyzed enamide hydrogenation are also reported.
Cite: Khiar, N., Navas, R., Álvarez González, E. y Fernández Fernández, I. (2008). New sulfur-phosphine ligands derived from sugars: synthesis and application in palladium-catalyzed allylic alkylation and in rhodium asymmetric hydrogenation. Arkivoc, 2008 (8), 211-224.
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URI: http://hdl.handle.net/11441/43143

DOI: 10.3998/ark.5550190.0009.817

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