Repositorio de producción científica de la Universidad de Sevilla

Pseudo enantiomeric mixed s/p ligands derived from carbohydrates for the 1,4-addition of phenyl boronic acid to cyclohexenone

 

Advanced Search
 
Opened Access Pseudo enantiomeric mixed s/p ligands derived from carbohydrates for the 1,4-addition of phenyl boronic acid to cyclohexenone
Cites

Show item statistics
Icon
Export to
Author: Valdivia Giménez, Victoria Esther
Bilbao Bustinza, Nerea
Moya, Juan Francisco
Rosales Barrios, C.
Salvador, Álvaro
Recio Jiménez, Rocío
Fernández Fernández, Inmaculada
Khiar, Noureddine
Department: Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica
Date: 2016
Published in: RSC Advances, 6 (4), 3041-3047.
Document type: Article
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
Cite: Valdivia Giménez, V.E., Bilbao Bustinza, N., Moya, J.F., Rosales Barrios, C., Salvador, Á., Recio Jiménez, R.,...,Khiar, N. (2016). Pseudo enantiomeric mixed s/p ligands derived from carbohydrates for the 1,4-addition of phenyl boronic acid to cyclohexenone. RSC Advances, 6 (4), 3041-3047.
Size: 708.3Kb
Format: PDF

URI: http://hdl.handle.net/11441/59961

DOI: 10.1039/c5ra10181f

See editor´s version

This work is under a Creative Commons License: 
Attribution-NonCommercial-NoDerivatives 4.0 Internacional

This item appears in the following Collection(s)