154473-89-9Relevant academic research and scientific papers
Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, amd Nitrones. A Convenient Route to Synthesis of β-Amino Alcohol
Shono, Tatsuya,Kise, Naoki,Fujimoto, Taku,Yamanami, Ayuko,Nomura, Ryoji
, p. 1730 - 1740 (2007/10/02)
The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode.The product, β-methoxyamino alcohol was easily converted to β-amino alcohol by simple reduction.A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime.The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction.Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.
