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

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

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 biary...

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Main Authors: Donglei Wang, Wei Liu, Mengyao Tang, Na Yu, Xiaoyu Yang
Format: Article
Language:English
Published: Elsevier 2019-12-01
Series:iScience
Online Access:http://www.sciencedirect.com/science/article/pii/S2589004219304742
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spelling doaj-32dbb5386bd14804a27581ee817650152020-11-24T23:51:17ZengElsevieriScience2589-00422019-12-0122195205Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and PhenolsDonglei Wang0Wei Liu1Mengyao Tang2Na Yu3Xiaoyu Yang4School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; University of Chinese Academy of Sciences, Beijing 100049, ChinaSchool of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; University of Chinese Academy of Sciences, Beijing 100049, ChinaSchool of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; University of Chinese Academy of Sciences, Beijing 100049, ChinaSchool of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, ChinaSchool of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China; Corresponding authorSummary: 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, Stereochemistryhttp://www.sciencedirect.com/science/article/pii/S2589004219304742
collection DOAJ
language English
format Article
sources DOAJ
author Donglei Wang
Wei Liu
Mengyao Tang
Na Yu
Xiaoyu Yang
spellingShingle Donglei Wang
Wei Liu
Mengyao Tang
Na Yu
Xiaoyu Yang
Atroposelective Synthesis of Biaryl Diamines and Amino Alcohols via Chiral Phosphoric Acid Catalyzed para-Aminations of Anilines and Phenols
iScience
author_facet Donglei Wang
Wei Liu
Mengyao Tang
Na Yu
Xiaoyu Yang
author_sort Donglei Wang
title 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_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_sort atroposelective synthesis of biaryl diamines and amino alcohols via chiral phosphoric acid catalyzed para-aminations of anilines and phenols
publisher Elsevier
series iScience
issn 2589-0042
publishDate 2019-12-01
description 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
url http://www.sciencedirect.com/science/article/pii/S2589004219304742
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AT weiliu atroposelectivesynthesisofbiaryldiaminesandaminoalcoholsviachiralphosphoricacidcatalyzedparaaminationsofanilinesandphenols
AT mengyaotang atroposelectivesynthesisofbiaryldiaminesandaminoalcoholsviachiralphosphoricacidcatalyzedparaaminationsofanilinesandphenols
AT nayu atroposelectivesynthesisofbiaryldiaminesandaminoalcoholsviachiralphosphoricacidcatalyzedparaaminationsofanilinesandphenols
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