A Versatile Method for Kinetic Resolution of Protecting‐Group‐Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation
Wei Liu, Qian Jiang, Xiaoyu Yang
Abstract
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.
Topics & Concepts
Kinetic resolutionPhosphoric acidCatalysisChemistryResolution (logic)Combinatorial chemistryProtecting groupChiral resolutionKinetic energyOptically activeGroup (periodic table)Organic chemistryEnantioselective synthesisComputational chemistryEnantiomerPhysicsQuantum mechanicsArtificial intelligenceAlkylComputer scienceAxial and Atropisomeric Chirality SynthesisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods