Literature DB >> 26662927

Combining Organocatalysis with Central-to-Axial Chirality Conversion: Atroposelective Hantzsch-Type Synthesis of 4-Arylpyridines.

Ophélie Quinonero1, Marion Jean1, Nicolas Vanthuyne1, Christian Roussel1, Damien Bonne1, Thierry Constantieux1, Cyril Bressy2, Xavier Bugaut3, Jean Rodriguez4.   

Abstract

Suitably substituted enantioenriched 4-aryl-1,4-dihydro-pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4-arylpyridines with central-to-axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model for the conversion of chirality is discussed.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  atropisomers; chiral conversion; enantioselectivity; organocatalysis; pyridines

Year:  2015        PMID： 26662927     DOI： 10.1002/anie.201509967

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Organocatalytic asymmetric arylation of indoles enabled by azo groups.

Authors:  Liang-Wen Qi; Jian-Hui Mao; Jian Zhang; Bin Tan
Journal:  Nat Chem       Date:  2017-10-02       Impact factor: 24.427

2.  Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides.

Authors:  Ryota Miyaji; Yuuki Wada; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  Beilstein J Org Chem       Date:  2017-08-02       Impact factor: 2.883

3.  Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones.

Authors:  Yong-Bin Wang; Sheng-Cai Zheng; Yu-Mei Hu; Bin Tan
Journal:  Nat Commun       Date:  2017-05-19       Impact factor: 14.919

4.  Organocatalytic atroposelective synthesis of axially chiral styrenes.

Authors:  Sheng-Cai Zheng; San Wu; Qinghai Zhou; Lung Wa Chung; Liu Ye; Bin Tan
Journal:  Nat Commun       Date:  2017-05-03       Impact factor: 14.919

5.  Organocatalytic atroposelective construction of axially chiral arylquinones.

Authors:  Shuai Zhu; Ye-Hui Chen; Yong-Bin Wang; Peiyuan Yu; Shao-Yu Li; Shao-Hua Xiang; Jun-Qi Wang; Jian Xiao; Bin Tan
Journal:  Nat Commun       Date:  2019-09-19       Impact factor: 14.919

6.  Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

Authors:  Yu-Long Hu; Zhe Wang; Hui Yang; Jie Chen; Zi-Bo Wu; Yibo Lei; Ling Zhou
Journal:  Chem Sci       Date:  2019-05-20       Impact factor: 9.825

7.  Stereoselective Synthesis of Atropisomeric Acridinium Salts by the Catalyst-Controlled Cyclization of ortho-Quinone Methide Iminiums.

Authors:  Xingxing Wu; Christof Sparr
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-25       Impact factor: 16.823

8.  Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.

Authors:  Xiaoze Bao; Jean Rodriguez; Damien Bonne
Journal:  Chem Sci       Date:  2019-11-20       Impact factor: 9.825
  8 in total

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