Kinetic Resolution of a Planar‐Chiral [2.2]Paracyclophane Derivative by Helical‐Peptide‐Catalyzed Michael Addition of Nitromethane

A resin-supported peptide catalyst was developed for kinetic resolution of a planar-chiral [2.2]paracyclophane derivative through Michael addition of nitromethane to an enone substituent on the paracyclophane structure. A helix-based peptide was effective to discriminate the planar chirality of the [2.2]paracyclophane structure, and to convert one enantiomer preferentially into the Michael adduct. By optimizing the peptide sequence at the N-terminus of the helical chain, highly enantioselective resolution was attained.