Kinetic Resolution of 1,<scp>2‐Diamines</scp>via Organocatalyzed Asymmetric Electrophilic Aminations of Anilines
Jinglei Xie, Zheng Guo, Wei Liu, Dekun Zhang, Yu‐Peng He, Xiaoyu Yang
Abstract
Comprehensive Summary An efficient kinetic resolution (KR) protocol for 1,2‐diamines has been developed through asymmetric electrophilic aminations of anilines enabled by chiral phosphoric acid catalysis. A wide array of substituted 1,2‐diamines were compatible with this method, generating both the recovered staring materials and the amination products with high enantioselectivities (with s ‐factor up to 218). Notably, this method is amenable to the kinetic resolution of 1,2‐diamines bearing α‐tertiary amine moieties, which represents the first KR of this type of 1,2‐diamines. Facile removal of the introduced hydrazine group and oxidative cleavage of the N ‐aryl group to release the free primary amine demonstrate the value of this method.