Palladium-Catalyzed Reductive Ring Opening with Formic Acid of Aziridines Bearing an α,β-Unsaturated Ester Group.

Abstract The palladium-catalyzed reduction of various N -arenesulfonylaziridines bearing α,β-unsaturated ester groups with formic acid and the stereochemistry of the reaction products have been investigated in detail. In all cases examined, (Z)-α,β-enoates, ( E )-α,β-enoates, and ( E )-β,γ-enoates bearing amino functionality at the δ-position were obtained. The formation of these three reduction products was taken as an indication that palladium-catalyzed isomerization occurs prior to the reduction step.