1. Pseudo enantiomeric mixed s/p ligands derived from carbohydrates for the 1,4-addition of phenyl boronic acid to cyclohexenone
- Author
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Noureddine Khiar, Alvaro Salvador, Juan Francisco Moya, Christian Rosales-Barrios, Victoria Valdivia, Nerea Bilbao, Inmaculada Fernández, Rocío Recio, and Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica
- Subjects
010405 organic chemistry ,Chemistry ,Stereochemistry ,General Chemical Engineering ,Heteroatom ,General Chemistry ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Cyclohexenone ,Reactivity (chemistry) ,Phenylboronic acid ,Enantiomer ,Boronic acid - Abstract
The 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
- Published
- 2016