Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect

A series of pyrrolidine-urea bifunctional organocatalysts was efficiently synthesized and applied to the asymmetric Michael addition of ketone to nitroolefin. Theoretical study was performed to shed light on the origin of their different activities and revealed that the rigid structure formed between catalyst 1b with nitroolefin via double hydrogen bonding retarded the approach of nucleophilic enamine intermediate.