Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions
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, e...
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| Published in | Chemical Society reviews Vol. 49; no. 1; pp. 286 - 3 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
02.01.2020
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| Subjects | |
| Online Access | Get full text |
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| 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.
We summarize in this review the recent development of chiral phosphoric acid (CPA)-catalyzed asymmetric dearomatization reactions. |
|---|---|
| AbstractList | 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.
We summarize in this review the recent development of chiral phosphoric acid (CPA)-catalyzed asymmetric dearomatization reactions. 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.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. 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. 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. |
| Author | Zheng, Chao You, Shu-Li Xia, Zi-Lei Xu-Xu, Qing-Feng |
| AuthorAffiliation | Chinese Academy of Sciences Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry State Key Laboratory of Organometallic Chemistry University of Chinese Academy of Sciences |
| AuthorAffiliation_xml | – sequence: 0 name: State Key Laboratory of Organometallic Chemistry – sequence: 0 name: Shanghai Institute of Organic Chemistry – sequence: 0 name: Center for Excellence in Molecular Synthesis – sequence: 0 name: University of Chinese Academy of Sciences – sequence: 0 name: Chinese Academy of Sciences |
| Author_xml | – sequence: 1 givenname: Zi-Lei surname: Xia fullname: Xia, Zi-Lei – sequence: 2 givenname: Qing-Feng surname: Xu-Xu fullname: Xu-Xu, Qing-Feng – sequence: 3 givenname: Chao surname: Zheng fullname: Zheng, Chao – sequence: 4 givenname: Shu-Li surname: You fullname: You, Shu-Li |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31829319$$D View this record in MEDLINE/PubMed |
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| Notes | Zi-Lei Xia was born in 1987 in Xuanwei, Yunnan province, China, and received his BS and MS degrees from the Tianjin University of Science and Technology in 2011 and China Pharmaceutical University in 2015, respectively. He joined the Shanghai Institute of Organic Chemistry (SIOC) and obtained his PhD degree under the supervision of Prof. Shu-Li You in 2018. His research was focused on chiral phosphoric acid-catalyzed asymmetric dearomatization reactions. Currently he is a postdoc research fellow at Purdue University with Prof. Arun K. Ghosh. Qing-Feng Xu-Xu was born in 1993 in Wuhan, Hubei province, China. He obtained his BS degree from Central China Normal University in 2015 and joined the Shanghai Institute of Organic Chemistry (SIOC) in the same year under the supervision of Prof. Shu-Li You. His research interests are dearomatization of arenes. Shu-Li You received his BSc in chemistry from Nankai University (1996). He then obtained his PhD from the Shanghai Institute of Organic Chemistry (SIOC) in 2001 under the supervision of Prof. Lixin Dai before doing postdoctoral studies with Prof. Jeffery Kelly at The Scripps Research Institute. From 2004, he worked at the Genomics Institute of the Novartis Research Foundation as a PI before returning to the SIOC as a Professor in 2006. He is currently the director of the State Key Laboratory of Organometallic Chemistry of the SIOC. His research interests mainly focus on asymmetric C-H functionalization and catalytic asymmetric dearomatization (CADA) reactions. He has published over 280 research papers in international peer-reviewed journals and edited two books. Chao Zheng was born in Hubei province, China in 1985. He studied chemistry and received his BSc degree at Shanghai Jiao Tong University in 2007. He obtained his PhD degree at the Shanghai Institute of Organic Chemistry (SIOC) under the supervision of Prof. Shu-Li You and Prof. Yu-Xue Li in 2012. Then he joined the group of Prof. Shu-Li You at the SIOC and was promoted to Associate Professor in 2015. His current work is focused on mechanistic understanding of homogeneous organic reactions by employing computational chemistry, and developing new catalytic asymmetric reactions. He has published over 40 journal papers and 4 book chapters. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
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| SubjectTerms | Aromatic compounds aromatic hydrocarbons Asymmetry benzofurans catalysts Chemical reactions Indoles isoquinolines Lewis acids Lewis bases naphthols Nucleophiles Organic compounds Phenols Phosphoric acid Pyridines quinolines |
| Title | Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions |
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