ELECTROORGANIC CHEMISTRY .144. ELECTROREDUCTIVE COUPLING OF KETONES WITH O-METHYL OXIMES, N,N-DIMETHYLHYDRAZONES, AND NITRONES - A CONVENIENT ROUTE TO SYNTHESIS OF BETA-AMINO ALCOHOL

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, beta-methoxyamino alcohol was easily converted to beta-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.