Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization
Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthes...
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| Published in | Nature communications Vol. 14; no. 1; pp. 3380 - 9 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
08.06.2023
Nature Publishing Group Nature Portfolio |
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| Online Access | Get full text |
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| Abstract | Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored.
Heterohelicenes are of increasing importance in materials science but organocatalytic enantioselective synthesis of these molecules remains challenging. Here, the authors synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization and explore the photochemical and electrochemical properties of these compounds. |
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| AbstractList | Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored.Heterohelicenes are of increasing importance in materials science but organocatalytic enantioselective synthesis of these molecules remains challenging. Here, the authors synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization and explore the photochemical and electrochemical properties of these compounds. Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored. Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored.Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored. Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored. Heterohelicenes are of increasing importance in materials science but organocatalytic enantioselective synthesis of these molecules remains challenging. Here, the authors synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization and explore the photochemical and electrochemical properties of these compounds. Abstract Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction of these molecules, especially by organocatalytic methods, is challenging, and few methods are available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed by oxidative aromatization. The method has a broad substrate scope and offers rapid access to an array of chiral quinohelicenes with enantioselectivities up to 99%. Additionally, the photochemical and electrochemical properties of selected quinohelicenes are explored. |
| ArticleNumber | 3380 |
| Author | Guo, Chenhao Li, Meng Ren, Zhiyuan Shao, Ying-Bo Gao, Xi Li, Chengwen Li, Xin |
| Author_xml | – sequence: 1 givenname: Chengwen surname: Li fullname: Li, Chengwen organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University – sequence: 2 givenname: Ying-Bo surname: Shao fullname: Shao, Ying-Bo organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University – sequence: 3 givenname: Xi surname: Gao fullname: Gao, Xi organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University – sequence: 4 givenname: Zhiyuan surname: Ren fullname: Ren, Zhiyuan organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University – sequence: 5 givenname: Chenhao surname: Guo fullname: Guo, Chenhao organization: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences – sequence: 6 givenname: Meng surname: Li fullname: Li, Meng organization: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences – sequence: 7 givenname: Xin orcidid: 0000-0001-6020-9170 surname: Li fullname: Li, Xin email: xin_li@nankai.edu.cn organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Haihe Laboratory of Sustainable Chemical Transformations |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37291164$$D View this record in MEDLINE/PubMed |
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| Snippet | Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However, enantioselective... Abstract Heterohelicenes are of increasing importance in the fields of materials science, molecular recognition, and asymmetric catalysis. However,... |
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| Title | Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization |
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