Construction of Axially Chiral Arylpyrroles via Atroposelective Diyne Cyclization
Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well‐established axially chiral 6‐membered biaryl skeletons, examples of 5‐membered biaryls have been quite scarce, and mono‐substituted 3...
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| Published in | Angewandte Chemie International Edition Vol. 62; no. 23; pp. e202303670 - n/a |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
05.06.2023
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well‐established axially chiral 6‐membered biaryl skeletons, examples of 5‐membered biaryls have been quite scarce, and mono‐substituted 3‐arylpyrrole atropisomers have not been reported. Here, we disclose a copper‐catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X−H insertion of vinyl cations. Importantly, this protocol not only represents the first synthesis of mono‐substituted 3‐arylpyrrole atropisomers, but also constitutes the first example of atroposelective diyne cyclization and the first atropisomer construction via vinyl cations. Theoretical calculations further support the mechanism of vinyl cation‐involved cyclization and elucidate the origin of enantioselectivity.
A novel copper‐catalyzed atroposelective diyne cyclization enables the efficient synthesis of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X−H insertion of vinyl cations. This method gives the first synthesis of mono‐substituted 3‐arylpyrrole atropisomers and the first atroposelective diyne cyclization. |
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| AbstractList | Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well‐established axially chiral 6‐membered biaryl skeletons, examples of 5‐membered biaryls have been quite scarce, and mono‐substituted 3‐arylpyrrole atropisomers have not been reported. Here, we disclose a copper‐catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X−H insertion of vinyl cations. Importantly, this protocol not only represents the first synthesis of mono‐substituted 3‐arylpyrrole atropisomers, but also constitutes the first example of atroposelective diyne cyclization and the first atropisomer construction via vinyl cations. Theoretical calculations further support the mechanism of vinyl cation‐involved cyclization and elucidate the origin of enantioselectivity. Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well-established axially chiral 6-membered biaryl skeletons, examples of 5-membered biaryls have been quite scarce, and mono-substituted 3-arylpyrrole atropisomers have not been reported. Here, we disclose a copper-catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X-H insertion of vinyl cations. Importantly, this protocol not only represents the first synthesis of mono-substituted 3-arylpyrrole atropisomers, but also constitutes the first example of atroposelective diyne cyclization and the first atropisomer construction via vinyl cations. Theoretical calculations further support the mechanism of vinyl cation-involved cyclization and elucidate the origin of enantioselectivity. Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well-established axially chiral 6-membered biaryl skeletons, examples of 5-membered biaryls have been quite scarce, and mono-substituted 3-arylpyrrole atropisomers have not been reported. Here, we disclose a copper-catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X-H insertion of vinyl cations. Importantly, this protocol not only represents the first synthesis of mono-substituted 3-arylpyrrole atropisomers, but also constitutes the first example of atroposelective diyne cyclization and the first atropisomer construction via vinyl cations. Theoretical calculations further support the mechanism of vinyl cation-involved cyclization and elucidate the origin of enantioselectivity.Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well-established axially chiral 6-membered biaryl skeletons, examples of 5-membered biaryls have been quite scarce, and mono-substituted 3-arylpyrrole atropisomers have not been reported. Here, we disclose a copper-catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X-H insertion of vinyl cations. Importantly, this protocol not only represents the first synthesis of mono-substituted 3-arylpyrrole atropisomers, but also constitutes the first example of atroposelective diyne cyclization and the first atropisomer construction via vinyl cations. Theoretical calculations further support the mechanism of vinyl cation-involved cyclization and elucidate the origin of enantioselectivity. Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to the well‐established axially chiral 6‐membered biaryl skeletons, examples of 5‐membered biaryls have been quite scarce, and mono‐substituted 3‐arylpyrrole atropisomers have not been reported. Here, we disclose a copper‐catalyzed atroposelective diyne cyclization for the construction of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X−H insertion of vinyl cations. Importantly, this protocol not only represents the first synthesis of mono‐substituted 3‐arylpyrrole atropisomers, but also constitutes the first example of atroposelective diyne cyclization and the first atropisomer construction via vinyl cations. Theoretical calculations further support the mechanism of vinyl cation‐involved cyclization and elucidate the origin of enantioselectivity. A novel copper‐catalyzed atroposelective diyne cyclization enables the efficient synthesis of a range of axially chiral arylpyrrole biaryls in good to excellent yields with generally excellent enantioselectivities via oxidation and X−H insertion of vinyl cations. This method gives the first synthesis of mono‐substituted 3‐arylpyrrole atropisomers and the first atroposelective diyne cyclization. |
| Author | Liu, Yi‐Xi Chen, Can‐Ming Zhou, Bo Xu, Zhou Chen, Yang‐Bo Liu, Li‐Gao Lu, Xin Ye, Long‐Wu |
| Author_xml | – sequence: 1 givenname: Yang‐Bo surname: Chen fullname: Chen, Yang‐Bo organization: Xiamen University – sequence: 2 givenname: Li‐Gao surname: Liu fullname: Liu, Li‐Gao organization: Xiamen University – sequence: 3 givenname: Can‐Ming surname: Chen fullname: Chen, Can‐Ming organization: Xiamen University – sequence: 4 givenname: Yi‐Xi surname: Liu fullname: Liu, Yi‐Xi organization: Xiamen University – sequence: 5 givenname: Bo surname: Zhou fullname: Zhou, Bo email: zhoubo@xmu.edu.cn organization: Xiamen University – sequence: 6 givenname: Xin surname: Lu fullname: Lu, Xin email: xinlu@xmu.edu.cn organization: Xiamen University – sequence: 7 givenname: Zhou surname: Xu fullname: Xu, Zhou organization: Xuzhou Medical University – sequence: 8 givenname: Long‐Wu orcidid: 0000-0003-3108-2611 surname: Ye fullname: Ye, Long‐Wu email: longwuye@xmu.edu.cn organization: Southern University of Science and Technology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36996038$$D View this record in MEDLINE/PubMed |
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| Keywords | BRONSTED ACID BINOL Heterocycles DESIGN Cyclizations ENANTIOSELECTIVE SYNTHESIS RESOLUTION 2+2+2 CYCLOADDITION INDOLES ATROPISOMERS YNAMIDES Asymmetric Catalysis Axial Chirality ACCESS Alkynes |
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| Snippet | Axially chiral biaryls widely exist in natural products and pharmaceuticals and are used as chiral ligands and catalysts in asymmetric synthesis. Compared to... |
| Source | Web of Science |
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| StartPage | e202303670 |
| SubjectTerms | Alkynes Asymmetric Catalysis Asymmetric synthesis Axial Chirality Catalysts Cations Chemical synthesis Chemistry Chemistry, Multidisciplinary Cyclizations Enantiomers Heterocycles Natural products Oxidation Physical Sciences Science & Technology Substitutes |
| Title | Construction of Axially Chiral Arylpyrroles via Atroposelective Diyne Cyclization |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202303670 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000977791900001 https://www.ncbi.nlm.nih.gov/pubmed/36996038 https://www.proquest.com/docview/2818563146 https://www.proquest.com/docview/2792908178 |
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