50485-71-7

Upstream product

• 116-54-1 dichloroacetic acid methyl ester 
• 100-52-7 benzaldehyde 
• 56014-20-1 methyl 2-chloro-3-oxo-3-phenylpropanoate 
• 16492-73-2 methyl erythro-3-acetoxy-2-chloro-3-phenylpropanoate 
• 96-34-4 methyl chloroacetate 
• 16715-03-0 methyl 2,2-dichloro-3-hydroxy-3-phenylpropanoate 
• 120235-89-4 methyl erythro-2-chloro-3-trichloroacetoxy-3-phenylpropanoate 
• 120235-88-3 methyl erythro-2-chloro-3-dichloroacetoxy-3-phenylpropanoate 
• 120235-87-2 methyl erythro-2-chloro-3-chloroacetoxy-3-phenylpropanoate 

Downstream Products

• 120235-89-4 methyl erythro-2-chloro-3-trichloroacetoxy-3-phenylpropanoate 
• 114642-84-1 methyl 3-bromo-2-chloro-3-phenylpropanoate 
• 120235-87-2 methyl erythro-2-chloro-3-chloroacetoxy-3-phenylpropanoate 
• 120235-88-3 methyl erythro-2-chloro-3-dichloroacetoxy-3-phenylpropanoate 

Relevant academic research and scientific papers

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

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.

A highly stereospecific synthesis of (E)-α,β-unsaturated esters

CrCl2-induced olefination of aldehydes using methyl dichloroacetate exclusively generates (E)-α,β-unsaturated esters in excellent yields. The intermediate α-chloro-β-hydroxy adducts could also be isolated in good yields under conditions of limited reagent.

Enantioselective ruthenium-mediated hydrogenation: Developments and applications

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.

AN ANOMALOUS COURSE OF THE DARZENS REACTION CATALYZED WITH MAGNESIUM METHOXIDE

The reaction of benzaldehyde with methyl chloroacetate catalyzed with magnesium methoxide gave beside the expected methyl 2,3-epoxy-3-phenylpropanoate (I) also comparable amounts of methyl 2-hydroxy-3-methoxy-3-phenylpropanoate (II).The condensation was accompanied by a competing disproportionation of benzaldehyde giving methyl benzoate and benzyl alcohol.The course of the condensation reaction is discussed.

Dehydroacetoxylation and Acetate Transesterification in the Reactions of erythro- and threo-Methyl 3-(Substituted acetoxy)-2-halogeno-3-phenylpropanoates with Triethylamine

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.