Access to Cyclic β-Amino Acids by Amine-Catalyzed Enantioselective Addition of the γ-Carbon Atoms of α,β-Unsaturated Imines to Enals

Disclosed herein is a new catalytic approach for an efficient access to cyclic beta-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote gamma-carbon atoms of alpha,beta-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic beta-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules.