This paper reports a general and efficient method for accessing 3,4-disubstituted succinimides through a dynamic kinetic resolution strategy based on asymmetric transfer hydrogenation. A Rh catalyst system exhibits high activities, enantioselectivities, and diastereoselectivities. Products with *syn*- and *anti*-configurations are obtained separately by controlling reaction conditions. Both the enol and imide groups can be reduced in N-unprotected substrates by controlling reaction time and catalyst loading. The reaction pathway and origin of stereoselectivity are elucidated by control experiments and theoretical calculations. This method offers a stereodivergent approach to enantioenriched succinimides.
