80255-23-8

Upstream product

• 1432589-65-5 C₁₅H₂₁NO₅ 
• 1255037-21-8 3-(4-methoxyphenyl)-2-nitropropan-1-ol 
• 79-24-3 Nitroethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 31236-71-2 lysichitalexin 
• 14425-64-0 4-methoxyphenethyl bromide 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 78551-14-1 2-nitro-2-propen-1-yl 2,2-dimethylpropanoate 

Downstream Products

• 1432589-22-4 (2S,4R)-2-isopropyl-5-(4-methoxyphenyl)-4-nitropentanal 

Relevant academic research and scientific papers

Cathodic hydrodimerization of nitroolefins

Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C-C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations at the acidic CH bond. Eight 1-aryl-2-nitro-1-propenes have been electrolyzed in an undivided electrolysis cell to afford 2,5-dinitro-3,4-diaryl hexanes in high yield. The 4-methoxy-, 4-trifluoromethyl-, 2-chloro- and 2,6-difluorophenyl group and furthermore the 2-furyl and 2-pyrrolyl group have been applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a β,β-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products.

Construction of chiral 2-substituted octahydroindoles from cyclic ketones and nitroolefins bearing only one α-substituent

A dual catalytic system has been developed following the screening of a series of chiral primary amine catalysts and chiral phosphoric acid catalysts for the Michael addition of cyclic ketones to nitroolefins bearing only one α-substituent. The resulting γ-nitro ketones, which contain a substituent on the carbon connected to the nitro group, were formed in excellent yields (>80%) with high levels of stereoselectivity (up to 94:6 dr and 98% ee) when the reaction was performed in benzene at 0 °C with 10 mol% of the optimal amine/phosphoric acid combination (1:1) as a catalyst. Subsequent reduction of the nitro group followed by intramolecular reductive amination could afford optically active cis-octahydroindole analogues bearing a non-functional substituent at their 2-position.

A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent

A series of α-substituted nitroolefins were employed in organocatalytic asymmetric Michael reactions with aldehydes. γ-Nitro carbonyl products were achieved in good yields (up to 86%) with good stereoselectivities (up to 96% ee and 24 : 1 dr). Reduction of the nitro group followed by intramolecular reductive amination successfully afforded various novel optically active 2,4-disubstituted pyrrolidine compounds.

32. 2'-Nitro-2'-propen-1'-yl 2,2-Dimethylpropanoate (NPP), A Multiple Coupling Reagent

The title compound 1 (NPP) is prepared from formaldehyde, nitromethane, and pivaloyl chloride.It is shown to be a versatile nitroallylating reagent combining with nucleophiles as different as anilines, indoles, enolates, and organolithium compounds.This i

NITROALLYLATION OF HIGHLY REACTIVE ORGANOLITHIUM COMPOUNDS BY 2-NITRO-3-PIVALOYLOXI-1-PROPENE (NPP)

The nitroolefin 1 (NPP) efficiently transfers a 2-nitroallyl group even to the most reactive nucleophilic centres of organolithium reagents to give the products of type 2 listed in the table.