117458-03-4

Upstream product

• 593-77-1 N-Methylhydroxylamine 
• 104-55-2 3-phenyl-propenal 
• 4229-44-1 N-methylhydroxyamine hydrochloride 

Downstream Products

• 1055424-77-5 5-benzo[1,3]dioxol-5-yl-2-methyl-3-styryl-2,3-dihydroisoxazole-4-carboxylic acid ethyl ester 
• 118149-91-0 (±)-methyl[(3E)-4-phenylbut-3-en-2-yl]amine 
• 1272565-02-2 C₁₇H₁₄O₄ 

Relevant academic research and scientific papers

BPh3-Catalyzed [2+3] Cycloaddition of Ph3PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties

A method for the generation of 5-isoxazolidinones with exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is proposed.

One-Pot Sequential [3 + 3] Dipolar Cycloaddition of Aldehyde or Ketone and Hydroxylamine with Spirocyclopropyl Oxindole

A Sc(OTf)3-catalyzed highly diastereoselective one-pot sequential [3 + 3] dipolar cycloaddition reaction of aldehyde or ketone, N-alkyl hydroxylamine, and spirocyclopropyl oxindole is developed, allowing facile construction of spirocyclic oxind

Dual Role of Pyrrolidine and Cooperative Pyrrolidine/Pyrrolidinium Effect in Nitrone Formation

The formation of nitrones by direct condensation between equimolecular amounts of N-substituted hydroxylamine hydrochlorides and aromatic or aliphatic aldehydes is efficiently promoted by pyrrolidine in a matter of minutes under very mild conditions in almost quantitative yields after a simple filtration through a short pad of silica gel. According to theoretical, spectroscopic, and experimental studies, this success is due to the ability of pyrrolidine to liberate the hydrochloride of the hydroxylamine and catalyze the reaction via iminium activation ion. Moreover, a cooperative pyrrolidine/pyrrolidinium chloride effect facilitates several steps of the catalytic cycle through proton transfer without hampering the nucleophilicity of the hydroxylamine by protonation.

Formaldehyde as Tethering Organocatalyst: Highly Diastereoselective Hydroaminations of Allylic Amines

Catalysts possessing sufficient activity to achieve intermolecular alkene hydroaminations under mild conditions are rare, and this likely accounts for the scarcity of asymmetric variants of this reaction. Herein, highly diastereoselective hydroaminations

1,3-Dipolar cycloadditions. Part-XV: Systematic spectroscopic investigations of C-aryl-N-methylnitrones

Several C-aryl-N-methylnitrones have been synthesised during the course of our work on 1,3-dipolar cycloadditions. Detailed systematic spectroscopic investigations of all these nitrones have been undertaken. These are reported along with some generalisati

1,3-Dipolar cycloadditions: Part VIII1-Microwave irradiation assisted synthesis of N-methyl-C-aryl nitrones

N-Methyl-C-arylnitrones have been synthesized in very high yields within a few minutes from N-methyl-hydroxylamine hydrochloride and aryl aldehydes in presence of sodium hydrogen carbonate in methylene chloride using the microwave irradiation technique.