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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Detalles Bibliográficos
Autores principales: Wang, Donglei, Liu, Wei, Tang, Mengyao, Yu, Na, Yang, Xiaoyu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6909093/
https://www.ncbi.nlm.nih.gov/pubmed/31785557
http://dx.doi.org/10.1016/j.isci.2019.11.024
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author Wang, Donglei
Liu, Wei
Tang, Mengyao
Yu, Na
Yang, Xiaoyu
author_facet Wang, Donglei
Liu, Wei
Tang, Mengyao
Yu, Na
Yang, Xiaoyu
author_sort Wang, Donglei
collection PubMed
description 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.
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spelling pubmed-69090932019-12-23 Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols Wang, Donglei Liu, Wei Tang, Mengyao Yu, Na Yang, Xiaoyu iScience Article 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. Elsevier 2019-11-16 /pmc/articles/PMC6909093/ /pubmed/31785557 http://dx.doi.org/10.1016/j.isci.2019.11.024 Text en © 2019 The Author(s) http://creativecommons.org/licenses/by-nc-nd/4.0/ This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Wang, Donglei
Liu, Wei
Tang, Mengyao
Yu, Na
Yang, Xiaoyu
Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
title Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
title_full Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
title_fullStr Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
title_full_unstemmed Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
title_short Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
title_sort atroposelective synthesis of biaryl diamines and amino alcohols via chiral phosphoric acid catalyzed para-aminations of anilines and phenols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6909093/
https://www.ncbi.nlm.nih.gov/pubmed/31785557
http://dx.doi.org/10.1016/j.isci.2019.11.024
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