A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation.

Wei LiuQianwen JiangXiaoyu Yang

Published in: Angewandte Chemie (International ed. in English) (2020)

A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.

Keyphrases

capillary electrophoresis
ionic liquid
room temperature
single molecule
highly efficient
mass spectrometry
quantum dots
climate change
multidrug resistant