N,N-Dicarboxymethyl hydrazine: an old but neglected reagent for chemoselective derivatization of carbonyl compounds

Abstract

N,N-Dicarboxymethyl hydrazine (DCMH) was found to be a chemoselective derivatization reagent of carbonyl compounds and its potential applications in organic synthesis was investigated for the first time. DCMH could be employed as a chemoselective protective reagent of aldehydes and gave the parent aldehydes in satisfactory yields. In proof-of-concept systems, DCMH could play the role of a scavenger to remove aldehydes in the presence of ketones. It was also used as a tagging reagent in the selective isolation of aldehyde from the complex mixture.