Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls
The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetri...
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| Published in | Nature communications Vol. 13; no. 1; pp. 632 - 9 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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London
Nature Publishing Group UK
02.02.2022
Nature Publishing Group Nature Portfolio |
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| Abstract | The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones.
There is great interest in methods for catalytic enantioselective construction of axially chiral compounds found in natural products. Here, the authors develop a cycloaddition strategy for atroposelective construction of indole-based biaryls via chiral phosphoric acid-catalysed cycloaddition. |
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| AbstractList | The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones. The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones. There is great interest in methods for catalytic enantioselective construction of axially chiral compounds found in natural products. Here, the authors develop a cycloaddition strategy for atroposelective construction of indole-based biaryls via chiral phosphoric acid-catalysed cycloaddition. The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones.The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones. The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole formation is an efficient method to construct indole-based biaryls. We report herein the result of a chiral phosphoric acid catalyzed asymmetric cycloaddition of 3-alkynylindoles with azonaphthalenes. A class of indole-based biaryls were prepared efficiently with excellent yields and enantioselectivities (up to 98% yield, 99% ee). Control experiment and DFT calculations illustrate a possible mechanism in which the reaction proceeds via a dearomatization of indole to generate an allene-iminium intermediate, followed by an intramolecular aza-Michael addition. This approach provides a convergent synthetic strategy for enantioselective construction of axially chiral heterobiaryl backbones.There is great interest in methods for catalytic enantioselective construction of axially chiral compounds found in natural products. Here, the authors develop a cycloaddition strategy for atroposelective construction of indole-based biaryls via chiral phosphoric acid-catalysed cycloaddition. There is great interest in methods for catalytic enantioselective construction of axially chiral compounds found in natural products. Here, the authors develop a cycloaddition strategy for atroposelective construction of indole-based biaryls via chiral phosphoric acid-catalysed cycloaddition. |
| ArticleNumber | 632 |
| Author | Zhang, Gong-Gu Zhou, Ling Hu, Wei Sun, Huai-Ri He, Rui-Qing Yu, Le Chen, Jie Yang, Sen Yang, Hui |
| Author_xml | – sequence: 1 givenname: Hui surname: Yang fullname: Yang, Hui organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 2 givenname: Huai-Ri surname: Sun fullname: Sun, Huai-Ri organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 3 givenname: Rui-Qing surname: He fullname: He, Rui-Qing organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 4 givenname: Le surname: Yu fullname: Yu, Le organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 5 givenname: Wei surname: Hu fullname: Hu, Wei organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 6 givenname: Jie surname: Chen fullname: Chen, Jie organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 7 givenname: Sen surname: Yang fullname: Yang, Sen organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 8 givenname: Gong-Gu surname: Zhang fullname: Zhang, Gong-Gu organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University – sequence: 9 givenname: Ling surname: Zhou fullname: Zhou, Ling email: zhoul@nwu.edu.cn organization: Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, National Demonstration Center for Experimental Chemistry Education, Northwest University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35110529$$D View this record in MEDLINE/PubMed |
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| Snippet | The axially chiral indole-aryl motifs are present in natural products and biologically active compounds as well as in chiral ligands. Atroposelective indole... There is great interest in methods for catalytic enantioselective construction of axially chiral compounds found in natural products. Here, the authors develop... |
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| SubjectTerms | 119/118 140/131 140/58 639/638/403 639/638/403/933 639/638/77/889 Bioactive compounds Biological activity Cycloaddition Enantiomers Humanities and Social Sciences Indoles multidisciplinary Natural products Phosphoric acid Science Science (multidisciplinary) |
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| Title | Organocatalytic cycloaddition of alkynylindoles with azonaphthalenes for atroposelective construction of indole-based biaryls |
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