28645-07-0

Upstream product

• 31508-44-8 2-phenylpropionic acid methyl ester 
• 7782-24-3 (S)-2-Phenylpropionic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 
• 3156-07-8 methyl phenyl ketene 
• 186581-53-3 diazomethane 
• 492-37-5 hydratropic acid 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 75-75-2 methanesulfonic acid 
• 492-38-6 2-phenylacrylic acid 
• 77-78-1 dimethyl sulfate 
• 7782-26-5 (R)-2-Phenylpropionic acid 
• 1865-29-8 2-phenyl-acrylic acid methyl ester 

Downstream Products

• 949560-41-2 (L)-2-phenylpropanehydrazide 
• 1350524-98-9 (L)-N-phenyl-2-(2-phenylpropanoyl)hydrazinecarbothioamide 
• 1123-85-9 (+)-(R)-2-phenylpropanol 
• 85020-76-4 methyl 2-deuterio-2-phenylpropionate 
• 73308-18-6 acetic acid (R)-(+)-2-phenyl-1-propanol ester 
• 93-53-8 (S)-2-phenyl-propionaldehyde 
• 145621-79-0 4-((S)-2-Acetoxy-1-methyl-ethyl)-benzoic acid methyl ester 
• 145621-80-3 methyl (S)-(-)-p-(2-hydroxy-1-methylethyl)benzoate 
• 145621-78-9 4-((S)-2-Acetoxy-1-methyl-ethyl)-benzoic acid 
• 145621-75-6 (S)-(-)-p-(2-acetoxy-1-methylethyl)benzyl alcohol 
• 145621-74-5 (S)-(-)-p-(2-acetoxy-1-methylethyl)benzyl chloride 
• 145621-77-8 Acetic acid (S)-2-(4-formyl-phenyl)-propyl ester 
• 145679-16-9 2--1-propanol 
• 93922-51-1 (S)-2-(4-methylphenyl)-1-propanol 

Relevant academic research and scientific papers

Alkylation of Aromatic Compounds with Optically Active Lactic Acid Derivatives: Synthesis of Optically Pure 2-Arylpropionic Acid Esters

The alkylation of benzene with (S)-methyl 2-- or 2-(mesyloxy)propionate, in the presence of aluminum chloride, affords (S)-methyl 2-phenylpropionate in good chemical (50-80percent) and excellent optical yield (97percent as determined by rotation), with inversion of configuration at the attacking carbon atom.

Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System

A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.

Synthetic method of chiral 2-aryl propionate

The invention belongs to the technical field of chemical synthesis, and relates to a synthetic method of chiral 2-aryl propionate, in particular to enantioselective synthesis of 2-aryl propionate. Thesynthetic method comprises the following steps: adding a copper salt, a chiral phosphine ligand, a silicon-hydrogen compound (in terms of SiH), ROH and 2-aryl acrylate in a certain ratio into a reaction bottle, carrying out a reaction in a reaction solvent at -50 to 40 DEG C for 0.25-6 h, and successively performing hydrolyzing, liquid separating, extracting, washing, drying and column chromatography after the reaction is finished, thereby obtaining the target compound 2-aryl propionate. Compared with the prior art, the method has the advantages that the 2-aryl acrylate is reduced by adopting a Cu catalytic system, a catalyst, namely a Cu compound is low in price, and the limitation of hydrogen high-pressure reduction and a noble metal catalyst is broken through. Chiral 2-aryl propionic acid can be obtained through a simple hydrolysis reaction of 2-aryl propionate, and a part of the compounds of 2-aryl propionate are effective components of current commercially-available drugs suchas ibuprofen and naproxen.

Nickel/Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling of Racemic α-Chloro Esters with Aryl Iodides

A unique nickel/organic photoredox co-catalyzed asymmetric reductive cross-coupling between α-chloro esters and aryl iodides is developed. This cross-electrophile coupling reaction employs an organic reductant (Hantzsch ester), whereas most reductive cross-coupling reactions use stoichiometric metals. A diverse array of valuable α-aryl esters is formed under these conditions with high enantioselectivities (up to 94 %) and good yields (up to 88 %). α-Aryl esters represent an important family of nonsteroidal anti-inflammatory drugs. This novel synergistic strategy expands the scope of Ni-catalyzed reductive asymmetric cross-coupling reactions.

Synthesis method of (S)-2-aryl propionate compound

The invention discloses a synthesis method of a (S)-2-aryl propionate compound. The (S)-2-aryl propionate compound shown in the formula IV is obtained by taking a compound shown in a formula I and a compound shown in a formula II as raw materials and reacting under the conditions of a chiral ligand shown in a formula III, a nickel catalyst, a photocatalyst, a reducing agent and alkali under the condition of visible light. The method has the advantages of cheap and easily available raw materials, convenient generation, mild conditions, environmental protection and safety, the photocatalyst canbe recycled, the production cost is greatly reduced, the test operation is simple, less waste is generated, and the method can be developed into an industrial production method.

Rhodium-Catalyzed Remote C(sp3)?H Borylation of Silyl Enol Ethers

A rhodium-catalyzed remote C(sp3)?H borylation of silyl enol ethers (SEEs, E/Z mixtures) by alkene isomerization and hydroboration is reported. The reaction exhibits mild reaction conditions and excellent functional-group tolerance. This method is compatible with an array of SEEs, including linear and branched SEEs derived from aldehydes and ketones, and provides direct access to a broad range of structurally diverse 1,n-borylethers in excellent regioselectivities and good yields. These compounds are precursors to various valuable chemicals, such as 1,n-diols and aminoalcohols.

Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP?, lithium arylborates are cross-coupled with tert-butyl α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP? is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs

The first cobalt-catalyzed enantioselective Negishi cross-coupling reaction, and the first arylation of α-halo esters with arylzinc halides, are disclosed. Employing a cobalt-bisoxazoline catalyst, various α-arylalkanoic esters were synthesized in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield). A diverse range of functional groups, including ether, halide, thioether, silyl, amine, ester, acetal, amide, olefin and heteroaromatics is tolerated by this method. This method was suitable for gram-scale reactions, enabling the synthesis of (R)-xanthorrhizol with high enantiopurity. Radical clock experiments support the intermediacy of radicals.

Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.