82079-51-4

Upstream product

• 67-56-1 methanol 
• 635-51-8 2-phenylsuccinic acid 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 29394-47-6 dimethyl (2E)-2-phenyl-2-butenedioate 
• 492-38-6 2-phenylacrylic acid 
• 29576-99-6 dimethyl 2-(phenyl)maleate 
• 186581-53-3 diazomethane 
• 725257-88-5 (2R,4R)-2-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester 
• 100-58-3 phenylmagnesium bromide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 624-49-7 dimethylfumarate 
• 98-80-6 phenylboronic acid 
• 4036-30-0 (S)-2-phenylsuccinic acid 

Downstream Products

• 164653-83-2 methanesulfonic acid (S)-4-methanesulfonyloxy-3-phenyl-butyl ester 
• 883901-37-9 (S)-3-(4-nitro-phenyl)-1-propyl-pyrrolidine 
• 883901-38-0 (S)-3-(4-amino-phenyl)-1-propyl-pyrrolidine 
• 883901-36-8 (S)-3-phenyl-1-propyl-pyrrolidine 
• 61548-78-5 (S)-(1,4-dibromobutan-2-yl)benzene 
• 6837-05-4 (2S)-2-phenylbutane-1,4-diol 

Relevant academic research and scientific papers

Asymmetric bis(alkoxycarbonylation) reaction of terminal olefins catalyzed by palladium in the presence of copper(I) triflate and a chiral bioxazoline ligand

A palladium-catalyzed asymmetric bis(alkoxycarbonylation) reaction of terminal olefins in the presence of copper(I) triflate was achieved by using a chiral bioxazoline ligand, (4S,4′S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro- 2,2′-bioxazole, under normal press

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

Stereoconvergent Reduction of Activated Alkenes by a Nicotinamide Free Synergistic Photobiocatalytic System

There is a growing interest in developing cooperative chemoenzymatic reactions to harness the reactivity of chemical catalysts and the selectivity of enzymes for the synthesis of nonracemic chiral compounds. However, existing chemoenzymatic systems with m

Autoinductive conversion of α,α-diiodonitroalkanes to amides and esters catalysed by iodine byproducts under O2

Studies to convert nitroalkanes into amides and esters using I2 and O2 revealed in situ-generated iodine species facilitate the homolytic C-I bond cleavage of α,α-diiodonitroalkanes, arguably in an autoinductive or autocatalytic manner. Consequently, we devised a rapid and economical I2/O2-based method to synthesise sterically hindered esters directly from primary nitroalkanes.

N,N-Dimethylformamide as Hydride Source in Nickel-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Esters

Asymmetric transfer hydrogenation of α,β-unsaturated esters is realized by using a nickel/bisphosphine catalyst and N,N-dimethylformamide (DMF) as the hydride source.

Nickel-catalyzed asymmetric transfer hydrogenation of conjugated olefins

Asymmetric transfer hydrogenation of electron-deficient olefins is realized with nickel catalysts supported by strongly σ-donating bisphosphines. Deuterium labeling experiments point to a reaction sequence of formate decarboxylation, asymmetric hydride in

Asymmetric hydrogenation of maleic acid diesters and anhydrides

Asymmetric hydrogenation of maleic and fumaric acid derivatives with iridium catalysts based on N,P ligands provides an efficient route to chiral enantioenriched succinates. A new catalyst derived from a 2,6-difluorophenyl- substituted pyridine-phosphinite ligand was developed and enables the conversion of a wide range of 2-alkyl and 2-arylmaleic acid diesters into the corresponding succinates in high enantiomeric purity. Mixtures of cis/trans substrates can be hydrogenated in an enantioconvergent fashion with high enantioselectivity, and further enhances the scope of this transformation. The products are valuable chiral building blocks with a structural motif found in many bioactive compounds, such as metalloproteinase inhibitors. An attractive enantioselective route to 2-alkyl- and 2-aryl-substituted succinic acid derivatives is opened up by the asymmetric hydrogenation of maleic and fumaric acid derivatives, using the new catalyst [Ir(cod)L]BArF, derived from a 2,6-difluorophenyl-substituted pyridine-phosphinite ligand. The products are valuable chiral building blocks having a structural motif found in many bioactive compounds. cod=1,5-cyclooctadiene.

Squaramide-catalyzed enantioselective Michael addition of masked acyl cyanides to substituted enones

Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective Michael addition to substituted enones. The reactions are catalyzed by chiral squaramides and afford adducts in high yields (90-99%) and with excellent enantioselectivities (85-98%). The addition products are unmasked to produce dicyanohydrins that, upon treatment with a variety of nucleophiles, provide γ-keto acids, esters, and amides. The use of this umpolung synthon has enabled, in enantiomerically enriched form, the first total synthesis of the prenylated phenol (+)-fornicin C.

Steric effects on the stereochemistry of old yellow enzyme-mediated reductions of unsaturated diesters: Flipping of the substrate within the enzyme active site induced by structural modifications

The ene-reductase-mediated reduction of the carbon-carbon double bond of some alkyl 2- substituted butenedioates was investigated. The stereochemical outcome of the reaction was found to be influenced by steric effects. Ethyl and butyl citraconates were converted into the corresponding alkyl (R)-2-methylsuccinates with excellent enantioselectivity, whereas ethyl and butyl mesaconates were completely unreactive. Methyl 2-substituted fumarates were reduced to enantiomerically enriched methyl (S)-2-substituted succinates, whereas the (Z)-stereoisomers were left unreacted by enereductases. Labelling experiments were performed to investigate the mechanism of these bioreductions and explain their stereochemical outcome.

Preparation of chiral 3-arylpyrrolidines via the enantioselective 1,4-addition of arylboronic acids to fumaric esters catalyzed by Rh(I)/chiral diene complexes

A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylbor