Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation

…, T Ayad, P Phansavath, V Ratovelomanana-Vidal…

Index: Prevost, Sebastien; Gauthier, Sebastien; De Andrade, Maria Cristina Cano; Mordant, Celine; Touati, Ali Rhida; Lesot, Philippe; Savignac, Philippe; Ayad, Tahar; Phansavath, Phannarath; Ratovelomanana-Vidal, Virginie; Genet, Jean-Pierre Tetrahedron Asymmetry, 2010 , vol. 21, # 11-12 p. 1436 - 1446

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Citation Number: 22

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 ...