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

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 aniline...

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Bibliographic Details
Published iniScience Vol. 22; pp. 195 - 205
Main Authors Wang, Donglei, Liu, Wei, Tang, Mengyao, Yu, Na, Yang, Xiaoyu
Format Journal Article
LanguageEnglish
Published United States Elsevier Inc 20.12.2019
Elsevier
Subjects
Organic Chemistry
Organic Synthesis
Stereochemistry
Organic Synthesis
Stereochemistry
Organic Chemistry
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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. [Display omitted] •Versatile methods for asymmetric synthesis of biaryl diamines and amino alcohols•Atroposelective para-aminations of biaryl anilines and phenols•Kinetic resolution of racemic biaryl anilines•Facile transformations of chiral products Organic Chemistry; Organic Synthesis; Stereochemistry
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These authors contributed equally
ISSN:2589-0042
2589-0042
DOI:10.1016/j.isci.2019.11.024