58502-68-4

Upstream product

• 98-83-9 isopropenylbenzene 
• 5670-65-5 (E)-1-nitro-2-phenyl-1-propene 
• 98-86-2 acetophenone 
• 705-60-2 1-phenyl-2-nitroprop-1-ene 
• 5670-65-5 1-nitro-2-phenylpropene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 66291-23-4 2-acetoxy-1-nitro-2-phenylpropane 

Downstream Products

• 7796-75-0 (+)-(R)-1-nitro-2-phenylpropane 
• 746647-15-4 (S)-1-nitro-2-phenylpropane 

Relevant academic research and scientific papers

Ag(I)-catalyzed synthesis of (E)-alkenyl phosphonates by oxidative coupling of H-phosphites with β-nitroolefins

A novel reaction constructing C(sp2)-P bond via the silver-catalyzed polarity-matched oxidative coupling of various H-phosphites with β-alkyl nitroolefins has been achieved. The reaction was performed by using acetonitrile as the solvent and Ni(NO3)2·6H2O as the oxidant, which could restrain unwanted isomerization of β-nitroolefins and selective produce (E)-alkenyl phosphonates in up to 83% yield.

Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones

The regiospecific radical reactions of β-alkyl nitroalkenes with sulfonyl hydrazides depended to a great extent on the choice of a solvent and catalyst. In the presence of dimethylformamide (DMF), β-alkyl nitroalkenes more likely converted into electron-rich allyl nitro compounds, which reacted with sulfonyl hydrazides to afford allyl sulfones with high regioselectivity. While in acetonitrile (CH3CN), vinyl sulfones were obtained directly via sulfonation of electron-deficient β-alkyl nitroalkenes. The mechanism investigation revealed that the regioselectivity was controlled by the equilibrium of β-alkyl nitroalkenes and allyl nitro compounds.

Allylic C-S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation

A metal-free, open-flask protocol was developed for the preparation of allylic sulfones through direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes. The key step of this process was the Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds. Through this process, the readily available conjugated nitroalkenes can be easily converted into allylic nitro compounds, which contain more reactive C=C bonds toward the sulfonyl radical addition. As a result, allylic sulfones were prepared in excellent yields with a broad substrate scope under mild conditions.

Enantioselective iridium-catalyzed hydrogenation of β,β-disubstituted nitroalkenes

An iridium complex with a newly prepared chiral spiro amino-phosphine ligand efficiently catalyzed the hydrogenation of both β-aryl-β-methyl-nitroalkenes and β-alkyl-β-methyl-nitroalkenes to the corresponding saturated nitroalkanes, which represents the f

Rh-catalyzed highly enantioselective hydrogenation of nitroalkenes under basic conditions

Go catalytic! A highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes and isomeric mixtures of nitroalkenes by using a Rh/DuanPhos catalytic system under basic conditions has furnished a convenient approach to β-chiral nitroalkanes, whic

A novel chiral bisphosphine-thiourea ligand for asymmetric hydrogenation of β,β-disubstituted nitroalkenes

A novel chiral bisphosphine-thiourea ligand was developed and applied in the highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes (up to 99% yield and 99% ee). With low catalytic loading (0.25 mol %), 98% ee and 98% conversion were obta

Peptide-catalyzed stereoselective conjugate addition reactions generating all-carbon quaternary stereogenic Centers

A powerful catalyst: Quaternary stereogenic centers adjacent to tertiary stereocenters were formed with high diastereoselectivities and enantioselectivities in conjugate addition reactions between aldehydes and β,β-disubstituted nitroolefins by using a peptidic catalyst (see scheme). γ-Amino acids and heterocyclic compounds bearing quaternary stereogenic centers are easily accessible from the products. Copyright

Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes

Building the building blocks: A highly enantioselective hydrogenation of ?-aryl-?-alkyl disubstituted nitroalkenes 1 has been developed. This method results in enantiomerically pure nitroalkanes 2, which are versatile precursors for chemical synthesis.

Chemoselective and enantioselective transfer hydrogenation of Β, Β-disubstituted nitroalkenes catalyzed by a water-insoluble chiral diaminerhodium complex in water

Asymmetric transfer hydrogenation of Β, Β-disubstituted nitroalkenes catalyzed by a chiral diaminerhodium complex in combination with HCO2NaHCO2H as a hydrogen source in water was successfully realized with high reactivity, excellent chemoselectivity and good enantioselectivity. The metal precursor and pH value of the aqueous solution have a large influence on the reactivity and chemoselectivity. The substituents on the benzene rings and the sulfonyl groups of TsDPEN have significant effects on the enantioselectivity. This catalytic asymmetric transformation is one of the most practical pathways to obtain optically active nitroalkanes.

Organocatalyzed enantioselective synthesis of nitroalkanes bearing all-carbon quaternary stereogenic centers through conjugate addition of acetone cyanohydrin

The first organocatalyzed phase-transfer enantioselective conjugate addition of cyanide ion derived from acetone cyanohydrin to β, β′-disubstituted nitroolefins is reported. The reaction leads to the efficient formation of nitroalkanes bearing an all-carb