615552-91-5

Upstream product

• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 7428-99-1 2-(4-methoxyphenyl)propan-2-ol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 19169-94-9 (E)-3-(4-methoxyphenyl)-2-butenoic acid 
• 19169-94-9 C₁₁H₁₂O₃ 

Downstream Products

• 748183-59-7 (S)-1-methoxy-4-(1-nitropropan-2-yl)benzene 
• 615552-98-2 (R)-1-methoxy-4-(1-nitropropan-2-yl)benzene 
• 70360-85-9 rac-1-methoxy-4-(1-nitropropan-2-yl)benzene 
• 1253909-46-4 C₁₀H₁₁⁽²⁾H₂NO₃ 
• 1253909-45-3 C₁₀H₁₂⁽²⁾HNO₃ 
• 1394330-87-0 (R)-2-(p-methoxyphenyl)propan-1-amine 
• 1415643-27-4 1-methoxy-4-(3-tosylprop-1-en-2-yl)benzene 
• 1182848-30-1 (E)-diethyl (2-(4-methoxyphenyl)prop-1-en-1-yl)phosphonate 

Relevant academic research and scientific papers

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

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.

Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers

Water enables new catalytic reactions for otherwise unreactive substrate systems. Under the “on water” reaction conditions, extremely unreactive β,β-disubstituted nitroalkenes smoothly underwent enantioselective Michael addition reactions with dithiomalonates using a chiral squaramide catalyst, affording both enantiomers of highly enantioenriched Michael adducts with all-carbon-substituted quaternary centers. The developed “on water” protocol was successfully applied for the scalable one-pot syntheses of chiral GABA analogs with all-carbon quaternary stereogenic centers at the β-position, which might show highly interesting pharmaceutical properties.

Fe(III)/Pyridine-Mediated Decarboxylative Nitration of α,β-Unsaturated Acids with Iron Nitrate

A novel and efficient method for the synthesis of (E)-nitroolefins in moderate to excellent yields is developed by Fe(III)/pyridine-mediated decarboxylative nitration of α,β-unsaturated acids with iron nitrate. A series of α,β-unsaturated acids are well tolerated in this procedure.

Substrate Scope Evaluation of the Enantioselective Reduction of β-Alkyl-β-arylnitroalkenes by Old Yellow Enzymes 1-3 for Organic Synthesis Applications

The substrate scope of the old yellow enzyme catalyzed reduction of β-alkyl-β-arylnitroalkenes is investigated. Compounds bearing either alkyl chains of increasing length at the carbon atom in position β to the nitro group or different substituents on the aromatic ring are prepared and submitted to bioreduction, to define the synthetic potential of this enantioselective reaction in the preparation of chiral fine chemicals. The versatility of the resulting nitroalkanes as chiral building blocks is shown by reducing the nitro group into a primary amine and by converting it into a carboxylic acid moiety by Meyer reaction. An "explosion" of chiral products can be observed by combining the highly enantioselective ene-reductase-mediated reduction of nitroalkenes with the chemical versatility of the nitro group.

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

Iridium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted Nitroalkenes

A highly efficient, iridium-catalyzed, enantioselective hydrogenation of β,β-disubstituted nitroalkenes has been developed. Using a complex consisting of iridium and (S,S)-f-spiroPhos as the catalyst, a variety of β,β-disubstituted nitroalkenes were successfully hydrogenated to the corresponding chiral nitroalkanes with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON=1000).

Synthesis of substituted nitroolefins: A copper catalyzed nitrodecarboxylation of unsaturated carboxylic acids

A novel, mild and convenient method for the nitrodecarboxylation of substituted cinnamic acid derivatives to their nitroolefins is achieved using a catalytic amount of CuCl (10 mol%) and tert-butyl nitrite (2 equiv.) as a nitrating agent in the presence of air. This reaction provides a useful method for the synthesis of β,β-disubstituted nitroolefin derivatives, which are generally difficult to access from other conventional methods. Additionally, this reaction is selective as the E-isomer of the acid derivatives furnishes the corresponding E-nitroolefins. One more salient feature of the method is, unlike other methods, no metal nitrates or HNO3 are employed for the transformation.

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.