Synthesis of Axially Chiral N‐Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Brønsted Acids
In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble‐metal catalysis. Herein, a facile access to axially chira...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 20; pp. e202201436 - n/a |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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09.05.2022
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| Edition | International ed. in English |
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| Abstract | In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble‐metal catalysis. Herein, a facile access to axially chiral N‐heterocycles enabled by chiral Brønsted acid‐catalyzed 5‐endo‐dig cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom‐economical synthesis of valuable N‐arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N‐arylindole skeletons are demonstrated to be applicable to asymmetric catalysis.
A chiral Brønsted acid‐catalyzed atroposelective cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method enables the practical and atom‐economical synthesis of valuable N‐arylindoles in excellent yields with generally excellent enantioselectivities. |
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| AbstractList | In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble‐metal catalysis. Herein, a facile access to axially chiral N‐heterocycles enabled by chiral Brønsted acid‐catalyzed 5‐endo‐dig cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom‐economical synthesis of valuable N‐arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N‐arylindole skeletons are demonstrated to be applicable to asymmetric catalysis.
A chiral Brønsted acid‐catalyzed atroposelective cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method enables the practical and atom‐economical synthesis of valuable N‐arylindoles in excellent yields with generally excellent enantioselectivities. In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble‐metal catalysis. Herein, a facile access to axially chiral N ‐heterocycles enabled by chiral Brønsted acid‐catalyzed 5‐ endo ‐ dig cyclization of ynamides is disclosed, which represents the first metal‐free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom‐economical synthesis of valuable N ‐arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N ‐arylindole skeletons are demonstrated to be applicable to asymmetric catalysis. In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble-metal catalysis. Herein, a facile access to axially chiral N-heterocycles enabled by chiral Brønsted acid-catalyzed 5-endo-dig cyclization of ynamides is disclosed, which represents the first metal-free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom-economical synthesis of valuable N-arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N-arylindole skeletons are demonstrated to be applicable to asymmetric catalysis. In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble-metal catalysis. Herein, a facile access to axially chiral N-heterocycles enabled by chiral Brønsted acid-catalyzed 5-endo-dig cyclization of ynamides is disclosed, which represents the first metal-free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom-economical synthesis of valuable N-arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N-arylindole skeletons are demonstrated to be applicable to asymmetric catalysis.In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble-metal catalysis. Herein, a facile access to axially chiral N-heterocycles enabled by chiral Brønsted acid-catalyzed 5-endo-dig cyclization of ynamides is disclosed, which represents the first metal-free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom-economical synthesis of valuable N-arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N-arylindole skeletons are demonstrated to be applicable to asymmetric catalysis. In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few examples on the synthesis of axially chiral compounds which exclusively relied on noble-metal catalysis. Herein, a facile access to axially chiral N-heterocycles enabled by chiral Bronsted acid-catalyzed 5-endo-dig cyclization of ynamides is disclosed, which represents the first metal-free protocol for the construction of axially chiral compounds from ynamides. This method allows the practical and atom-economical synthesis of valuable N-arylindoles in excellent yields with generally excellent enantioselectivities. Moreover, organocatalysts and ligands based on such axially chiral N-arylindole skeletons are demonstrated to be applicable to asymmetric catalysis. |
| ArticleNumber | 202201436 |
| Author | Wang, Ze‐Shu Liu, Bin‐Yang Li, Cui‐Ting Hong, Xin Zhu, Lu‐Jing Ye, Long‐Wu |
| Author_xml | – sequence: 1 givenname: Ze‐Shu surname: Wang fullname: Wang, Ze‐Shu organization: Xiamen University – sequence: 2 givenname: Lu‐Jing surname: Zhu fullname: Zhu, Lu‐Jing organization: Westlake University – sequence: 3 givenname: Cui‐Ting surname: Li fullname: Li, Cui‐Ting organization: Xiamen University – sequence: 4 givenname: Bin‐Yang surname: Liu fullname: Liu, Bin‐Yang organization: Xiamen University – sequence: 5 givenname: Xin surname: Hong fullname: Hong, Xin email: hxchem@zju.edu.cn organization: Westlake University – sequence: 6 givenname: Long‐Wu orcidid: 0000-0003-3108-2611 surname: Ye fullname: Ye, Long‐Wu email: longwuye@xmu.edu.cn organization: Chinese Academy of Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35246909$$D View this record in MEDLINE/PubMed |
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| Keywords | Heterocycles ASYMMETRIC-SYNTHESIS ENANTIOSELECTIVE SYNTHESIS REACTIVITY SULFONAMIDES DEPROTECTION Organocatalysis INDOLES Bronsted Acids Axial Chirality CONSTRUCTION C-C ACCESS Alkynes Brønsted Acids |
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| Snippet | In recent years, asymmetric catalysis of ynamides has attracted much attention, but these reactions mostly constructed central chirality, except for a few... |
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| SubjectTerms | Alkynes Asymmetry Axial Chirality Brønsted Acids Catalysis Chemistry Chemistry, Multidisciplinary Chirality Heterocycles Organocatalysis Physical Sciences Science & Technology |
| Title | Synthesis of Axially Chiral N‐Arylindoles via Atroposelective Cyclization of Ynamides Catalyzed by Chiral Brønsted Acids |
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