Article
New sulfur-phosphine ligands derived from sugars: synthesis and application in palladium-catalyzed allylic alkylation and in rhodium asymmetric hydrogenation
Author/s | Khiar, Noureddine
Navas, Raquel Álvarez González, Eleuterio Fernández Fernández, Inmaculada |
Department | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica |
Publication Date | 2008 |
Deposit Date | 2016-07-05 |
Published in |
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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 ... 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. |
Project ID. | CTQ2006- 15515-CO2-01
CTQ2007-61185 P06-FQM-01852 P07- FQM-2774 |
Citation | 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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