950478-12-3

Upstream product

• 101671-00-5 (E)-2-(4-methylphenyl)-1-nitroethene 
• 75-24-1 trimethylaluminum 
• 947383-46-2 (E)-1-methyl-4-(1-nitroprop-1-en-2-yl)benzene 
• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 90922-14-8 1-Nitro-2-p-tolyl-propen-⁽¹⁾ 
• 122-00-9 para-methylacetophenone 
• 1197-01-9 p-cymene-8-ol 

Relevant academic research and scientific papers

Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.

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.

Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins

This paper focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action is supported by mechanistic investigations.

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.

Transfer hydrogenation in water: Enantioselective, catalytic reduction of (E)-β,β-disubstituted nitroalkenes

A mild catalytic asymmetric transfer hydrogenation of β,β- disubstituted nitroalkenes Is reported. Formic acid Is used as a reductant in combination with an Ir catalyst. The reaction Is conducted in water at low pH and open to air to give adducts In prepa

Optically active nitrile oxides: synthesis and 1,3-dipolar cycloaddition reactions

Baker's yeast-promoted reduction of the C{double bond, long}C bond in 2-aryl-1-nitropropenes gave the corresponding optically active (R)-2-aryl-1-nitropropanes of high enantiomeric purity (ee >90%). They were next converted with the aid of the Mukaiyama and Hoshino method into the optically active nitrile oxides, which were made to react in situ with ethyl propiolate, methylvinyl ketone and (R)-1-phenyl-2-(phenylsulfonyl)ethyl acrylate to yield the appropriate, enantiomerically enriched, isoxazoles or 4,5-dihydroisoxazoles as diastereomeric mixtures, respectively.

Organocatalytic asymmetric transfer hydrogenation of nitroolefins

We describe a highly efficient and highly enantioselective Hantzsch ester mediated conjugate transfer hydrogenation of β,β-disubstituted nitroolefins that is catalyzed by a Jacobsen-type thiourea catalyst. Copyright

Cu-catalysed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-ibuprofen

Trimethylaluminium undergoes enantioselective (ee up to 93%) copper-catalysed Michael addition to various nitroalkenes. Copper thiophenecarboxylate (CuTC) (2 mol %) and 4 mol % of a chiral phosphoramidite ligand are sufficient for a complete and clean reaction. The synthesis of (+)-ibuprofen is described with 82% ee.