TY - JOUR
T1 - Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates
T2 - Hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation
AU - Prévost, Sébastien
AU - Gauthier, Sébastien
AU - De Andrade, Maria Cristina Caño
AU - Mordant, Céline
AU - Touati, Ali Rhida
AU - Lesot, Philippe
AU - Savignac, Philippe
AU - Ayad, Tahar
AU - Phansavath, Phannarath
AU - Ratovelomanana-Vidal, Virginie
AU - Genêt, Jean Pierre
PY - 2010/6/23
Y1 - 2010/6/23
N2 - The dynamic kinetic resolution (DKR) of racemic α-chloro β-ketoesters and α-chloro β-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding α-chloro β-hydroxyesters and α-chloro β- hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere® which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, 13C NMR in chiral oriented solvents was used to investigate the DKR effect.
AB - The dynamic kinetic resolution (DKR) of racemic α-chloro β-ketoesters and α-chloro β-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding α-chloro β-hydroxyesters and α-chloro β- hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere® which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, 13C NMR in chiral oriented solvents was used to investigate the DKR effect.
U2 - 10.1016/j.tetasy.2010.05.017
DO - 10.1016/j.tetasy.2010.05.017
M3 - Article
AN - SCOPUS:77956649773
SN - 0957-4166
VL - 21
SP - 1436
EP - 1446
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 11-12
ER -
