Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
Donglei Wang,
Wei Liu,
Mengyao Tang,
Na Yu,
Xiaoyu Yang
Affiliations
Donglei Wang
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; University of Chinese Academy of Sciences, Beijing 100049, China
Wei Liu
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; University of Chinese Academy of Sciences, Beijing 100049, China
Mengyao Tang
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; University of Chinese Academy of Sciences, Beijing 100049, China
Na Yu
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China
Xiaoyu Yang
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; Corresponding author
Summary: A versatile method for atroposelective synthesis of chiral biaryl diamines and amino alcohols has been developed via para-amination of anilines and phenols with azodicarboxylates enabled by chiral phosphoric acid catalysis. Meanwhile, highly efficient kinetic resolution of the racemic biaryl anilines has also been realized through these reactions, giving selectivity factor up to 246. The gram-scale reaction and facile derivatizations of the chiral products well demonstrate the potential of these reactions in the development of novel chiral ligands and catalysts. : Organic Chemistry; Organic Synthesis; Stereochemistry Subject Areas: Organic Chemistry, Organic Synthesis, Stereochemistry
