114030-75-0

Upstream product

• 67-56-1 methanol 
• 635-51-8 2-phenylsuccinic acid 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 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 
• 624-49-7 dimethylfumarate 
• 98-80-6 phenylboronic acid 
• 29394-47-6 dimethyl (2E)-2-phenyl-2-butenedioate 
• 100-58-3 phenylmagnesium bromide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 29576-99-6 dimethyl 2-(phenyl)maleate 
• 725257-89-6 (2S,4S)-2-[(4S)-4-isobutyl-2-oxo-1,3-oxazolidin-3-yl]-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester 

Downstream Products

• 46292-93-7 R-(+)-phenylsuccinic acid 
• 61548-78-5 (S)-(1,4-dibromobutan-2-yl)benzene 
• 6837-05-4 (2S)-2-phenylbutane-1,4-diol 
• 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 

Relevant academic research and scientific papers

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.

Phosphine sulfides: Novel effective ligands for the palladium-catalyzed bisalkoxycarbonylation of olefins

Phosphine sulfides were found to be effective as a ligand in the palladium(II)-catalyzed bisalkoxycarbonylation of olefins. Aromatic olefins and vinylsilanes were converted into the corresponding succinates in high yields under mild conditions. Enantiosel

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

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.

A general platinum-catalyzed alkoxycarbonylation of olefins

Hydroxy- and alkoxycarbonylation reactions constitute important industrial processes in homogeneous catalysis. Nowadays, palladium complexes constitute state-of-the-art catalysts for these transformations. Herein, we report the first efficient platinum-catalysed alkoxycarbonylations of olefins including sterically hindered and functionalized ones. This atom-efficient catalytic transformation provides straightforward access to a variety of valuable esters in good to excellent yields and often with high selectivities. In kinetic experiments the activities of Pd- and Pt-based catalysts were compared. Even at low catalyst loading, Pt shows high catalytic activity.

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.

Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides

Asymmetric hydrogenation of various 3-substituted maleic anhydrides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) under mild conditions was successfully developed. A wide range of 3-alkyl and 3-aryl maleic anhydrides were hydrogenated well to provide the desired products 3-substituted succinic anhydrides in one hour with excellent results (full conversions, up to 99% yield, 99% ee, 3000 TON). Importantly, we developed a creative and efficient synthetic route to construct the key intermediate of the hypoglycemic drug mitiglinide through our catalytic system.

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.