Asymmetric Two‐Component Alkenyl Catellani Reaction for the Construction of C—N Axial Chirality
Comprehensive Summary Herein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. Various partially aromatic iodinated 2‐pyridones, q...
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| Published in | Chinese journal of chemistry Vol. 42; no. 7; pp. 699 - 704 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY‐VCH Verlag GmbH & Co. KGaA
01.04.2024
Wiley Wiley Subscription Services, Inc |
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| Online Access | Get full text |
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| Abstract | Comprehensive Summary
Herein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. Various partially aromatic iodinated 2‐pyridones, quinolones, coumarin and uracil substrates react with 2,6‐disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C—N atropisomers (38 examples, up to 97% e.e.). The obtained C—N axial chirality originates from the preformed transient C—C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C—N atropisomers through a N‐deprotection and aromatization sequence. In addition, a remote axial‐to‐central diastereoinduction process dictated by C—N axial chirality is observed with excellent diastereocontrol.
An asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality is reported. This method is based on a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. |
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| AbstractList | Herein, we report an asymmetric two-component alkenyl Catellani reaction for the construction of C-N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial-to-axial chirality transfer process. Various partially aromatic iodinated 2-pyridones, quinolones, coumarin and uracil substrates react with 2,6-disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C-N atropisomers (38 examples, up to 97% e.e.). The obtained C-N axial chirality originates from the preformed transient C-C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C-N atropisomers through a N-deprotection and aromatization sequence. In addition, a remote axial-to-central diastereoinduction process dictated by C-N axial chirality is observed with excellent diastereocontrol. Herein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. Various partially aromatic iodinated 2‐pyridones, quinolones, coumarin and uracil substrates react with 2,6‐disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C—N atropisomers (38 examples, up to 97% e.e. ). The obtained C—N axial chirality originates from the preformed transient C—C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C—N atropisomers through a N‐deprotection and aromatization sequence. In addition, a remote axial‐to‐central diastereoinduction process dictated by C—N axial chirality is observed with excellent diastereocontrol. Comprehensive Summary Herein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. Various partially aromatic iodinated 2‐pyridones, quinolones, coumarin and uracil substrates react with 2,6‐disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C—N atropisomers (38 examples, up to 97% e.e.). The obtained C—N axial chirality originates from the preformed transient C—C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C—N atropisomers through a N‐deprotection and aromatization sequence. In addition, a remote axial‐to‐central diastereoinduction process dictated by C—N axial chirality is observed with excellent diastereocontrol. An asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality is reported. This method is based on a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. Comprehensive SummaryHerein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene cooperative catalysis and an axial‐to‐axial chirality transfer process. Various partially aromatic iodinated 2‐pyridones, quinolones, coumarin and uracil substrates react with 2,6‐disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C—N atropisomers (38 examples, up to 97% e.e.). The obtained C—N axial chirality originates from the preformed transient C—C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C—N atropisomers through a N‐deprotection and aromatization sequence. In addition, a remote axial‐to‐central diastereoinduction process dictated by C—N axial chirality is observed with excellent diastereocontrol. |
| Author | Jiao, Yinchun Wu, Chenggui Liu, Ze‐Shui Shang, Yong Deng, Shuang Cong, Hengjiang Zhou, Qianghui Liu, Chang Cheng, Hong‐Gang |
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| Copyright | 2023 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH 2024 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH |
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| Keywords | AROMATIC FUNCTIONALIZATION Heterocycles PALLADIUM ENANTIOSELECTIVE SYNTHESIS ANNULATION Atropisomerism STEREOCHEMICAL RELAY Asymmetric catalysis PD/NORBORNENE Axial-to-axial chirality transfer H FUNCTIONALIZATION NORBORNENE Alkenyl Catellani reaction REGIOSELECTIVE SYNTHESIS ARYL IODIDES |
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Herein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a... Herein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a palladium/chiral norbornene... Herein, we report an asymmetric two-component alkenyl Catellani reaction for the construction of C-N axial chirality through a palladium/chiral norbornene... Comprehensive SummaryHerein, we report an asymmetric two‐component alkenyl Catellani reaction for the construction of C—N axial chirality through a... |
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| SubjectTerms | Alkenyl Catellani reaction Asymmetric catalysis Asymmetry Atropisomerism Axial‐to‐axial chirality transfer Bromides Catalysis Chemistry Chemistry, Multidisciplinary Chirality Coumarin Heterocycles Palladium Physical Sciences Quinoline Quinolones Science & Technology Substrates Uracil |
| Title | Asymmetric Two‐Component Alkenyl Catellani Reaction for the Construction of C—N Axial Chirality |
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