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The electrochemical reduction of imazapyr at the static mercury drop electrode was studied by cyclic voltammetry as a function of pH in aqueous buffered media. The process leads to the 2,3-C=N double bond reduction in the imidazoline moiety in all media. The products have been isolated by controlled-potential electrolyses and identified by high performance liquid chromatography-tandem mass spectrometry measurements and 1 H-NMR, 13 C-NMR, and IR spectra. Although no chiral auxiliary was used, a moderate diasteroisomeric excess was observed. The diasteromeric ratio depends on pH of the electrolyses.

Stereoselective Electrochemical Reduction of Imazapyr in Aqueous Media Without Chiral Auxiliaries