Copper‐Catalyzed Enantioselective Dehydro‐Diels–Alder Reaction: Atom‐Economical Synthesis of Axially Chiral Carbazoles
The dehydro‐Diels–Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper‐catalyzed enantioselective DDA reaction through v...
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| Published in | Angewandte Chemie International Edition Vol. 63; no. 51; pp. e202411709 - n/a |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
16.12.2024
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| Edition | International ed. in English |
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| Abstract | The dehydro‐Diels–Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper‐catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom‐economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non‐noble metal‐catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis.
A copper‐catalyzed enantioselective dehydro‐Diels–Alder reaction has been realized via vinyl cation pathway, enabling the atom‐economical synthesis of axially chiral phenyl and indolyl carbazoles. This protocol continues the first example of non‐noble metal‐catalyzed enantioselective DDA reaction. Notably, the constructed axially chiral carbazoles are applicable to asymmetric catalysis. |
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| AbstractList | The dehydro-Diels-Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper-catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom-economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non-noble metal-catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis. The dehydro‐Diels–Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper‐catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom‐economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non‐noble metal‐catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis. A copper‐catalyzed enantioselective dehydro‐Diels–Alder reaction has been realized via vinyl cation pathway, enabling the atom‐economical synthesis of axially chiral phenyl and indolyl carbazoles. This protocol continues the first example of non‐noble metal‐catalyzed enantioselective DDA reaction. Notably, the constructed axially chiral carbazoles are applicable to asymmetric catalysis. The dehydro-Diels-Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper-catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom-economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non-noble metal-catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis.The dehydro-Diels-Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper-catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom-economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non-noble metal-catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis. The dehydro‐Diels–Alder (DDA) reaction is a powerful method for the construction of aromatic compounds. However, the enantioselective DDA reaction has been rarely developed, probably due to the competitive thermal reaction. Herein, we report a copper‐catalyzed enantioselective DDA reaction through vinyl cation pathway. The reaction leads to the atom‐economical synthesis of axially chiral phenyl and indolyl carbazoles in generally excellent yields with good to excellent atroposelectivities. This methodology represents the first example of non‐noble metal‐catalyzed enantioselective DDA reaction. Notably, new chiral ligand and organocatalyst derived from the constructed axially chiral carbazole are demonstrated to be useful in asymmetric catalysis.Dedicated to Professor Yong Tang on the occasion of his 60th birthday. |
| Author | Chen, Hua‐Hong Zhou, Bo Gao, Jun‐Zhe Chen, Yang‐Bo Ye, Long‐Wu |
| Author_xml | – sequence: 1 givenname: Hua‐Hong surname: Chen fullname: Chen, Hua‐Hong organization: Xiamen University – sequence: 2 givenname: Yang‐Bo surname: Chen fullname: Chen, Yang‐Bo organization: Xiamen University – sequence: 3 givenname: Jun‐Zhe surname: Gao fullname: Gao, Jun‐Zhe organization: Xiamen University – sequence: 4 givenname: Long‐Wu surname: Ye fullname: Ye, Long‐Wu organization: Chinese Academy of Sciences – sequence: 5 givenname: Bo orcidid: 0000-0002-5551-678X surname: Zhou fullname: Zhou, Bo email: zhoubo@xmu.edu.cn organization: Xiamen University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39267546$$D View this record in MEDLINE/PubMed |
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| Keywords | DDA Reaction Heterocycles STYRENES INSERTION REAGENTS Ynamides RESOLUTION ATROPISOMERS CYCLOADDITION Asymmetric Catalysis Axial Chirality ACCESS ALKALOIDS DIYNES |
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| SubjectTerms | Aromatic compounds Asymmetric Catalysis Axial Chirality Carbazole Carbazoles Catalysis Chemical synthesis Chemistry Chemistry, Multidisciplinary Copper DDA Reaction Diels-Alder reactions Enantiomers Heterocycles Noble metals Physical Sciences Science & Technology Ynamides |
| Title | Copper‐Catalyzed Enantioselective Dehydro‐Diels–Alder Reaction: Atom‐Economical Synthesis of Axially Chiral Carbazoles |
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