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Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation |
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| Authors: | Sébastien Prévost Sébastien Gauthier Maria Cristina Caño de Andrade Céline Mordant Ali Rhida Touati Philippe Lesot Philippe Savignac Tahar Ayad Phannarath Phansavath Virginie Ratovelomanana-Vidal Jean-Pierre Genêt |
| Institution: | 1. Laboratoire Charles Friedel UMR CNRS 7223, Chimie ParisTech ENSCP, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France;2. Faculté des Sciences, Laboratoire de Synthèse Organique et Photochimie, Avenue de l’Environnement, 5000 Monastir, Tunisia;3. RMN en Milieu Orienté, ICMMO, UMR CNRS 8182, Université Paris Sud 11, Bât. 410, F-91405 Orsay Cedex, France;4. 146 Allée de la Clairière 91190 Gif-sur-Yvette, France |
| Abstract: | 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. |
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