1067494-87-4

Upstream product

• 26954-35-8 1-(4-methoxyphenyl)pent-4-en-1-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2475-92-5 4-methoxyacetophenone oxime 
• 106-95-6 allyl bromide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 113579-77-4 1-(4-methoxy-phenyl)-pent-4-en-1-ol 

Downstream Products

• 1067494-92-1 1-(4-methoxyphenyl)pent-4-en-1-one O-2-phenylacetyl oxime 
• 91640-13-0 5-(4-methoxyphenyl)-2-methyl-3,4-dihydro-2H-pyrrole 
• 161064-07-9 3-(4-methoxyphenyl)-5-vinylisoxazoline 
• 1101835-41-9 C₂₆H₂₈N₂O₆ 

Relevant academic research and scientific papers

Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.

Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification

A straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines is realized by Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of a commercially available bisphosphine ligand. The enantioenriched products can be facilely converted to functionalized alcohols with high fidelity of chiral transfer.

Iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines

Herein, a new method of iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines has been developed. By using readily available substrates, 32 examples of functionalized pyrrolines were prepared in moderate to good yields. Notably, examples of reduction and cycloaddition reactions of the obtained product were given as well. This journal is

Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development

The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.

Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization

The treatment of an O-(4-methoxybenzyl) oxime ether bearing an olefin substituent and 1-chloroanthraquinone (1-Cl-AQN) catalyst in 2-butanone under visible-light irradiation affords pyrroline via an iminyl radical intramolecular hydroimination. Mechanistic studies indicate that iminyl radical generation mainly proceeds by hydrogen abstraction of the photocatalyst from the benzyl position of the oxime. Moreover, the hydrogen atom was identified in circulation from the benzylic position of the substrates between AQN and 2-butanone to quench the carbon radical without requiring any additional reagents.

From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals

Dioxime oxalates are useful precursors for the clean generation of iminyl radicals by sensitised UV photolysis and can be adapted for serviceable preparations of 3,4-dihydro-2H-pyrroles and phenanthridines. The Royal Society of Chemistry.

Thermal rearrangement of indolyl oxime esters to pyridoindoles

(Chemical Equation Presented) Acyl oximes derived from a variety of indolylalkanones underwent a ring closure sequence during FVP to afford 9H-pyrido[2,3-b]indoles. Unlike UV light promoted reactions of oxime esters, the mechanism is almost certainly not mediated by iminyl radicals but probably involves tautomerism, elimination of acetic acid, and a final electrocyclic ring closure.