Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines.

ABSTRACT: The stereoselective electroreductive intramolecular coupling of chiral diimines of aromatic aldehydes with trans-1,2-diaminocyclohexane for the synthesis of enantiopure tetrasubstituted piperazines has been investigated by an electrochemical approach. The methodology was successfully developed under both batch and continuous flow conditions, and afforded enantiomerically pure products with complete stereoselectivity. Substrates bearing electron-donating or electron-withdrawing groups on the aromatic rings provided good to excellent yields, indicating that both types of substituents are well tolerated under the reaction conditions. Although modest yields were obtained under flow conditions, the continuous process afforded higher productivities and space-time yields than the batch rea

SUBMITTER: Gazzotti M 

PROVIDER: S-EPMC12434927 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature