158243-49-3

Upstream product

• 636-82-8 cyclohexene-1-carboxylic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 17497-53-9 1-iodo-1-cyclohexene 
• 201230-82-2 carbon monoxide 
• 36278-22-5 1-cyclohexenoyl chloride 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 

Downstream Products

• 7157-78-0 5-(1-Cyclohexenyl)-3-methylisoxazole 
• 62672-77-9 1-(cyclohexen-1-yl)-2-propen-1-one 
• 55170-16-6 1-(1-cyclohexenyl)-2-methylprop-2-en-1-one 
• 72846-34-5 C₉H₁₀O 
• 1591812-59-7 C₁₈H₂₀O 
• 1591812-46-2 C₁₈H₂₂O₂ 
• 1591812-45-1 C₂₀H₂₄O₂ 

Relevant academic research and scientific papers

Hydroxylamine catalyzed Nazarov cyclizations of divinyl ketones Dedicated to Professor Hilton Weiss on his 80th birthday

The first examples of iminium catalyzed Nazarov cyclizations of divinyl ketones are presented. Experiments describing hydroxylamine catalysis of the cyclization of eight α-alkoxy divinyl ketones (60-79% yield) and one unactivated divinyl ketone (38% yield) are reported. Phenyl substitution at the β-position of the divinyl ketone inhibits cyclization, whereas β-alkyl substituted α-alkoxy divinyl ketones readily cyclize.

High-yielding synthesis of Weinreb amides via homogeneous catalytic carbonylation of iodoalkenes and iodoarenes

Iodoarenes (iodobenzene and 2-iodothiophene) and iodoalkenes (1-iodocyclohexene, 1-iodo-4-tert-butylcyclohexene, 1-iodo-2-methylcyclohexene and 1-iodo-1-(1-naphthyl)ethene) were used as substrates in palladium-catalysed aminocarbonylation with N,O-dimethylhydroxylamine. The corresponding Weinreb amides were prepared in high isolated yields (up to 87%) when forcing conditions (40-60 bar of CO, 50 °C) were used. The aminocarbonylation provides the Weinreb amides as pure products in a chemoselective reaction. No formation of ketocarboxamides, due to double CO insertion, except for 2-iodothiophene, was observed even at 60 bar of CO pressure.

Synthesis of Weinreb amides via Pd-catalyzed aminocarbonylation of heterocyclic-derived triflates

(Chemical Equation Presented) The direct transformation of lactam-, lactone-, and thiolactone-derived triflates into N-methoxy-N-methyl or morpholine Weinreb amides has been realized using Pd-catalyzed aminocarbonylation under CO atmospheric pressure and