Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols

被引：19
|
作者：
Wang, Donglei [1 ,2 ]
Liu, Wei [1 ,2 ]
Tang, Mengyao [1 ,2 ]
Yu, Na [1 ]
Yang, Xiaoyu [1 ]
机构：
[1] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ISCIENCE | 2019年 / 22卷
关键词：
ELECTRON-RICH ARENES; ENANTIOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; BRONSTED ACID; ASYMMETRIC-SYNTHESIS; AXIAL CHIRALITY; BOND FORMATION; BINOL; ATROPISOMERS; 2-NAPHTHOLS;
D O I：
10.1016/j.isci.2019.11.024
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
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.
引用
收藏
页码：195 / +
页数：159
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