New sulfur-phosphine ligands derived from sugars: synthesis and application in palladium-catalyzed allylic alkylation and in rhodium asymmetric hydrogenation
Description
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.
Abstract
Dirección General de Investigaciones Científicas y Técnicas CTQ2006- 15515-CO2-01 y CTQ2007-61185
Abstract
Junta de Andalucía P06-FQM-01852 y P07- FQM-2774
Abstract
Fundación Ramón Areces
Additional details
- URL
- https://idus.us.es/handle/11441/43143
- URN
- urn:oai:idus.us.es:11441/43143
- Origin repository
- USE