126374-24-1

Upstream product

• 25310-30-9 2-(3-methoxyphenyl)propanenitrile 
• 64-18-6 formic acid 
• 768-70-7 1-ethynyl-3-methoxybenzene 
• 2398-37-0 3-methoxyphenyl bromide 
• 86358-29-4 ethyl 2‐(3‐methoxyphenyl)‐2‐oxoacetate 
• 35840-01-8 ethyl m-methoxy-atropate 
• 133033-15-5 2-(3-methoxyphenyl)acrylic acid 

Downstream Products

• 127641-46-7 (S)-2-(3-Methoxy-phenyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

The Reaction of Chiral Nucleophiles with Organomanganese Arene Complexes

The reaction of the enolate derived from chiral N-acyloxazolidinone (1) and organomanganese arene complexes (2) gives η5-dienyl complexes (3) which can be converted into chiral 2-arylpropionic acids by cleavage of the chiral auxiliary and oxidation of the η5-dienyl moiety.

Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens

We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

Enantioselective hydrolysis of various racemic α-substituted arylacetonitriles using Rhodococcus sp. CGMCC 0497

The enantioselective hydrolysis of 17 racemic α-substituted arylacetonitriles by Rhodococcus sp. CGMCC 0497 is described. The corresponding (R)-amides and (S)-acids were obtained with excellent enantiomeric excess in most cases. The effect of steric and electronic factors on the outcome of the reactions are discussed here. The results prove that nitrile-converting enzymes are efficient tools for the synthesis of sterically unencumbered chiral α-arylpropionic acids and amides.

Manufacture of optically active α-arylalkanoic acids and precursors thereof

This invention concerns a new process of preparing optically active α-arylalkanoic acids and their precursors. These α-arylalkanoic acids, esters, amides, nitriles, oxazolines and metal salts are stereoselectively prepared by forming the metal or metal halide of the corresponding acid, ester, amide, oxazoline, nitrile, or metal salt and treating the compound so prepared with an aryl halide in the presence of a chiral (optically active) transition metal catalyst of the formula (LL*)QZT wherein Q is a transition metal selected from palladium and nickel; Z and T are independently halogen; and LL* is a chiral tertiary diphosphine compound capable of acting as a bidentate ligand with Q to form a 5-membered ring, optionally in the presence of a dipolar aprotic solvent or mixtures thereof, for a time sufficient to form the corresponding optically active α-arylalkanoic acid, ester, amide, nitrile, oxazoline or metal salt, and optionally concomitantly or sequentially hydrolyzing any ester, amide, nitrile, oxazoline or metal salt formed to the corresponding optically active α-arylalkanoic acid. The process optionally further includes removal of halogen atom from the aromatic portion of the α-arylalkanoic acid. The process optionally includes subsequent formation of the pharmaceutically acceptable salts and esters of the optionally active α-arylalkanoic acid. This is a simple process for the preparation of the described optically active α-arylalkanoic acids. These compounds are useful as pharmaceutical (e.g., anti-inflammatory) agents.