Literature DB >> 31829319

Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions.

Zi-Lei Xia1, Qing-Feng Xu-Xu1, Chao Zheng1, Shu-Li You1.   

Abstract

We summarize in this review the recent development of chiral phosphoric acid (CPA)-catalyzed asymmetric dearomatization reactions. A wide array of electron-rich arenes (indoles, phenols, naphthols, benzothiophenes, benzofurans, etc.) and electron-poor arenes (pyridines, quinolines, isoquinolines, etc.) has been proved reactive towards various reaction partners in the presence of a CPA catalyst, enabling asymmetric dearomatization reactions that lead to structurally-diverse polycyclic molecules. The reactions are grouped according to the roles of the arenes in the reactions (as nucleophiles or electrophiles) and the types of reaction partners. This review closes with a personal perspective on the dynamic research area of asymmetric dearomatization reactions by CPAs.

Entities:  

Year:  2019        PMID: 31829319     DOI: 10.1039/c8cs00436f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  5 in total

Review 1.  Phosphorus-Based Catalysis.

Authors:  Changmin Xie; Andrew J Smaligo; Xian-Rong Song; Ohyun Kwon
Journal:  ACS Cent Sci       Date:  2021-03-16       Impact factor: 14.553

2.  Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis.

Authors:  Wen-Jun Zhou; Zhe-Hao Wang; Li-Li Liao; Yuan-Xu Jiang; Ke-Gong Cao; Tao Ju; Yiwen Li; Guang-Mei Cao; Da-Gang Yu
Journal:  Nat Commun       Date:  2020-06-29       Impact factor: 14.919

3.  Molecular insights into chirality transfer from double axially chiral phosphoric acid in a synergistic enantioselective intramolecular amination.

Authors:  Soumi Tribedi; Raghavan B Sunoj
Journal:  Chem Sci       Date:  2021-12-29       Impact factor: 9.825

4.  Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization.

Authors:  Hiroki Tanaka; Naoya Ukegawa; Muhammet Uyanik; Kazuaki Ishihara
Journal:  J Am Chem Soc       Date:  2022-03-23       Impact factor: 15.419

5.  Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement.

Authors:  Qiu Shi; Zhehui Liao; Zhili Liu; Jiajia Wen; Chenguang Li; Jiamin He; Jiazhen Deng; Shan Cen; Tongxiang Cao; Jinming Zhou; Shifa Zhu
Journal:  Nat Commun       Date:  2022-07-29       Impact factor: 17.694

  5 in total

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