111197-94-5

Upstream product

• 186581-53-3 diazomethane 
• 4842-49-3 (R)-2-(4-methoxyphenyl)propionic acid 
• 50415-73-1 methyl 2-(4-methoxyphenyl)propionate 
• 94703-61-4 (4-methoxy-phenyl)-methyl-malonic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 23197-67-3 diethyl 2-(4-methoxyphenyl)malonate 
• 696-62-8 para-iodoanisole 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 74-88-4 methyl iodide 
• 51747-42-3 2-(4-methoxy-phenyl)-acrylic acid 
• 121-97-1 4-Methoxypropiophenone 
• 149-73-5 trimethyl orthoformate 
• 103593-54-0 (S)-2-methylsulfonyloxy-1-(4-methoxyphenyl)-1-propanone dimethyl acetal 

Downstream Products

• 93397-63-8 (S)-4-methoxy-β-methylbenzeneethanol 
• 147922-82-5 (S)-2-(p-Methoxyphenyl)propanal 
• 147879-04-7 (4S,5R,6S)-2,4-Dimethyl-5-hydroxy-6-(p-methoxyphenyl)-1-hepten-3-one 
• 148215-93-4 (3R,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1-heptene-3,5-diol 
• 147879-07-0 (2S,3S,4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-1,3,5-heptanetriol 
• 147922-83-6 (4S,5R,6S)-2,4-Dimethyl-6-(p-methoxyphenyl)-5-(trimethylsiloxy)-1-hepten-3-one 
• 147879-12-7 (3R,4S,5R,6S)-2,4-Dimethyl-5-<(2-methoxyethoxy)methoxy>-6-(p-methoxyphenyl)-1-hepten-3-ol 

Relevant academic research and scientific papers

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.

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.

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.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

Enantioselective hydrogenation of α-substituted acrylic acids catalyzed by iridium complexes with chiral spiro aminophosphine ligands

Highly active: Iridium complexes with chiral spiro aminophosphine ligands were synthesized and applied as catalysts for the asymmetric hydrogenation of α-substituted acrylic acids (see scheme). The complexes were highly active catalysts, showing turnover frequencies of up to 6000 h-1, and catalyst loadings could be reduced to 0.01 mol %. Copyright

Pd/Josiphos-catalyzed enantioselective α-arylation of silyl ketene acetals and mechanistic studies on transmetalation and enantioselection

Palladium/(4-MeO-3,5-MePh)2PF-Pcy2) catalyzed the enantioselective arylation of silyl ketene acetals with iodoarenes in the presence of TlOAc to promote transmetalation of silyl ketene acetals. The highest enantioselectivities giving α-arylesters up to 91% ee were achieved when (E)-1-methoxy-1-(trimethylsiloxy)propene (E/Z = 88/12) was used for the silyl ketene acetal. The effect on enantioselection of a chiral ligand is discussed on the basis of the X-ray structure of the palladium/(4-MeO-3,5- MePh)2PF-Pcy2) complex and results of DFT computational studies on mechanistic aspects of the catalytic cycle.

Asymmetric intermodular heck-type reaction of acyclic alkenes via oxidative palladium(II) catalysis

Herein, we report an asymmetric intermolecular Heck-type reaction of acyclic alkenes by using a palladium-pyridinyl oxazoline diacetate complex under oxidative palladium(II) catalysis conditions. A premade palladium-ligand complex afforded higher enantioselectivities than a corresponding premixed palladium-ligand system, while offering enhanced asymmetric induction when compared to known intermolecular Heck-type protocols.

MICROBIAL HYDROLYSIS AS A POTENT METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE NITRILES, AMIDES AND CARBOXYLIC ACIDS

Many kinds of aromatic nitriles have been hydrolyzed to afford the corresponding amides and carboxylic acids, by the aid of enzyme system of Rhodococcus butanica.This enzymatic hydrolysis can be successfully applied to the kinetic resolution of α-arylpropionitriles, resulting in the formation of (R)-amides and (S)-carboxylic acids.

Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

PPL catalyzed monohydrolysis of 2-aryl substituted 13-propanediol diacetates afforded the corresponding monoacetates in acceptable to fair chemical and optical yields. Electronic effects in the aromatic ring were examined. Elaboration of some 2-arylpropanediol monoacetates to optically active 2-arylpropanols and propanoic acids was performed.