Enzyme Mimics for Michael Additions with Novel Proton Transport Groups

Molecular receptors with an enzyme‐like behavior in the Michael addition of pyrrolidine to an α,β‐unsaturated lactam have been designed. Catalytic activities are discussed and related to the substrate association constants. Chiral assistance of enantiomerically pure receptors was also investigated. One of the receptors shows a 4:1 enantiomeric ratio (60 % ee) for the addition of pyrrolidine and 3‐pyrroline.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) Oxyanion hole‐like structures and novel proton‐transfer groups are combined in the design of molecular receptors showingenzyme‐like behaviour.