Kinetic Resolution of 1,2‐Diamines via Organocatalyzed Asymmetric Electrophilic Aminations of Anilines

作者：Xie Jinglei; Guo Zheng; Liu Wei; Zhang Dekun; He YuPeng; Yang Xiaoyu

来源：Chinese Journal of Chemistry, 2022, 40(14): 3025-3025.

DOI：10.1002/cjoc.202290245

• Asymmetric catalysis
• 1,2‐Diamines
• Kinetic resolution
• Chiral phosphoric acids
• Amination

Comprehensive Summary(#br)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. (#br)A novel kinetic resolution (KR) protocol for 1,2‐diamines has been developed through asymmetric electrophilic aminations of anilines enabled by chiral phosphoric acid catalysis. Notably, 1,2‐diamines bearing both α‐secondary and α‐tertiary amine moieties are compatible with this method, which gave good to high KR performances (with s‐factor up to 218).

• 单位
  精细化工国家重点实验室; 中国科学院大学