Oxazolidinone to succinamide: a novel rearrangement reaction

During the course of an investigative work with a monosubstituted succinic acid half-ester tethered to a chiral oxazolidinone, an unexpected disubstituted succinimide was obtained with a high degree of stereoselectivity as the major product. Subsequent investigative work confirmed the structure and further defined the scope of this rearrangement reaction.