37504-79-3

Upstream product

• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 108-24-7 acetic anhydride 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 108-05-4 vinyl acetate 
• 3480-87-3 3-hydroxy-3-phenylpropanoic acid 
• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 100-52-7 benzaldehyde 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 876-27-7 4-chlorophenyl acetate 

Relevant academic research and scientific papers

Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst

The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

Lipases A and B from Candida antarctica in the enantioselective acylation of ethyl 3-heteroaryl-3-hydroxypropanoates: Aspects on the preparation and enantiopreference

The preparative scale kinetic resolution of racemic ethyl 2- and 3-furyl- and 2- and 3-thienyl-3-hydroxypropanoates has been performed by Candida antarctica lipases A and B with vinyl esters. A study based on the present work together with the literature has been carried out in terms of lipase enantiopreference and substrate structure. We also discuss the excellent behavior of the lipase A in O-acylations of secondary alcohols with respect to enantiopreference.

Thermomorphic system with non-fluorous phase-tagged Ru(BINAP) catalyst: Facile liquid/solid catalyst separation and application in asymmetric hydrogenation

The thermomorphic BINAP derivative 1 tagged with long alkyl chains was prepared from (S)-5,5′-diamino BINAP and applied to Ru-catalyzed asymmetric hydrogenation of β-ketoesters under homogeneous conditions in 3:1 (v/v) ethanol/ 1,4-dioxane at 60 °C with high enantioselectivity (up to 98% ee). Results indicated that the Ru(1) catalyst was easily recovered by simple cooling and precipitation and could be used for at least four cycles without any loss of enantioselectivity.

Synthesis of Novel Diastereomeric Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation Reactions

(Matrix Presented) Diastereomeric biaryl diphosphine ligands 10 and 11 with added chiral centers on the backbone were synthesized. Substrate-directed asymmetric synthesis occurred in the coupling step of the preparation of the diastereomeric diphosphine oxides. The diastereomeric diphosphine oxides were easily separated by column chromatography with silica gel. Ruthenium catalysts containing these ligands were highly effective in the hydrogenation of 2-(6′-methoxy-2′-naphthyl)propenoic acid and β-ketoesters. The additional chiral centers had a significant influence on the enantioselectivity and activity of the catalysts.

Enantioselective synthesis of beta-hydroxy acid derivatives via a one-pot aldol reaction-dynamic kinetic resolution.

[reaction: see text]. Combining dynamic kinetic resolution with an aldol reaction provides access to beta-hydroxy ester derivatives with high enantiomeric purity (up to 99% ee) in a one-pot procedure. Only simple starting materials are required in this enantioselective process, and preformation of a silyl enol ether is not necessary.