50485-71-7Relevant articles and documents
Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: Hemisynthesis of Taxotere through Ru-DIFLUORPHOS asymmetric hydrogenation
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
experimental part, p. 1436 - 1446 (2010/11/03)
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.
Enantioselective ruthenium-mediated hydrogenation: Developments and applications
Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre
, p. 163 - 171 (2007/10/03)
A general preparation of chiral ruthenium(II) catalysts and the homogeneous enantioselective hydrogenation of prochiral olefins and keto groups are presented. Some applications to the synthesis of biologically active compounds are reported.
Dehydroacetoxylation and Acetate Transesterification in the Reactions of erythro- and threo-Methyl 3-(Substituted acetoxy)-2-halogeno-3-phenylpropanoates with Triethylamine
Garay, Raul O.,Cabaleiro, Mercedes C.
, p. 1643 - 1648 (2007/10/02)
The response of the rate of triethylamine-induced dehydroacetoxylation of methyl threo-3-acetoxy-2-halogeno-3-phenylpropanoate to the influence of substituents in the leaving group points to a change in mechanism from (E1cB)I to a concerted process of the carbanion type.On the other hand, the erythro-isomers seem to undergo elimination exclusively through a carbanionic pathway.The effect of the acetoxy substituents upon the competitive transesterification is discussed.