74592-10-2

Upstream product

• 1075-77-0 (E)-4-chlorocinnamic aldehyde 

Downstream Products

• 74592-07-7 trans-4-(p-Chlorophenyl)-3-butenylamine Hydrochloride 
• 1065515-05-0 (2R,3R,E)-5-(4-chlorophenyl)-2-isopropyl-3-(nitromethyl)pent-4-enal 
• 1374343-98-2 (S,E)-5-(4-chlorophenyl)-3-(nitromethyl)-1-phenylpent-4-en-1-one 
• 1374343-99-3 (S,E)-6-(4-chlorophenyl)-4-(nitromethyl)hex-5-en-2-one 
• 74592-05-5 trans-N-<4-(p-Chlorphenyl)-3-butenyl>phthalimide 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.

Enantio- and regioselective conjugate addition of organometallic reagents to linear polyconjugated nitroolefins

The copper-catalysed conjugate addition of trialkylaluminium and dialkylzinc reagents to polyconjugated nitroolefins (nitrodiene and nitroenyne derivatives) is reported. A reversed Josiphos ligand L7 allows for the selective 1,4- or 1,6-addition with high enantioselectivities. Copyright

Organocatalytic "difficult" michael reaction of ketones with nitrodienes utilizing a primary amine-thiourea based on Di-tert-butyl aspartate

The primary amine-thiourea based on di-tert-butyl (S)-aspartate and (1R,2R)-1,2-diphenylethylene-1,2-diamine has been successfully employed in the "difficult" Michael reaction between aromatic ketones or acetone with nitrodienes. The high stability and re

Organocatalyzed conjugate addition of carbonyl compounds to nitrodienes/nitroenynes and synthetic applications

The purpose of this study is to point out the synthetic utility of a new class of Michael acceptors (nitrodienes and nitroenynes). The highly enantioselective organocatalytic Michael addition of carbonyl compounds to these functionalized nitroolefins has been carried out in the presence of (S)-diphenylprolinol silyl ether to achieve some interesting building blocks in high selectivities. The adducts thus obtained can be easily converted by taking advantage of the corresponding unsaturated carbon-carbon bond. In presence of the double bond, metathesis or electrophilic activation could be carried out whereas in the presence of the triple bond electrophilic acti-vation could be conducted. We thus focused on a gold-catalyzed cyclization of the bis-homopropargylic alcohol to afford the corresponding substituted tetrahydrofuran. Then, we also demonstrated that organic and gold catalysts were compatible in a one-pot process. Indeed, we developed a one-pot enantioselective organocatalytic Michael addition to a nitroenyne followed by a gold-catalyzed acetalization/cyclization to achieve tetrahydrofuranyl ethers in high diastereoand enantioselectivities with excellent yields.

Enantioselective and regiodivergent copper-catalyzed conjugate addition of trialkylaluminium reagents to extended nitro-michael acceptors

(Figure presented) The first highly enantioselective and regiodivergent conjugate addition of trialkylaluminium reagents to nitrodienes and nitroenynes is described. By a design of the substrate and a fine-tuning of the reaction conditions, it is possible to selectively form the 1,4- or 1,6-adduct. The same combination of catalyst, copper source, and a ferrocene-based phosphine ligand afforded enantioselectivities up to 95% and 91%, respectively.

Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes

(Chemical Equation Presented) The asymmetric organocatalyzed Michael addition of aldehydes to α,β-γ,δ-unsaturated nitro compounds has been accomplished using only 5 mol % of (S)-diphenylprolinol silyl ether and 2 equiv of aldehyde in a mixture of ethanol and water (5% v/v). The Michael adducts were obtained in good yields, diastereoselectivities up to 94/6, and ee's up to 99%. This process provides synthetically useful compounds which can easily lead to more complex molecules, as exemplified with substituted tetrahydropyran or cyclohexene.