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Pseudo Enantiomeric Mixed S/P Ligands Derived from Carbohydrates for the 1,4-Addition of Phenyl Boronic Acid to Cyclohexenone

AutorValdivia, Victoria ; Bilbao, N.; Moya, F.J.; Salvador, A.; Fernández, I.; Khiar el Wahabi, Noureddine
Fecha de publicación2016
EditorRoyal Society of Chemistry (Great Britain)
CitaciónRSC Advances, 6: 3041-3047 (2016)
ResumenThe application of phosphinite-thioglycosides and phosphine-thioglycosides ligands in the Rh(I)-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone is reported. Among the ligands tested, phosphinite-thioglycoside 3 and phosphine-thioglycoside 10, bearing a 1,2-cis arrangement of the two heteroatoms, have exhibited the best results in terms of reactivity and enantioselectivity. Interestingly, ligands 3 and 10, both derived from D-sugar are able to generate the addition product of the phenylboronic acid to the cyclohexenone with opposite configuration, behaving thus as enantiomers
Versión del editorhttp://dx.doi.org/ 10.1039/C5RA10181F
URIhttp://hdl.handle.net/10261/128743
DOI10.1039/C5RA10181F
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