Regio- and Atroposelective Ring-Opening of 1H-Benzo[4,5]oxazolopyridinones
© 2024 Wiley‐VCH GmbH..
The development of new methods for regio- and stereoselective activation of C-O bonds in ethers holds significant promise for synthetic chemistry, offering advantages in terms of environmental sustainability and economic efficiency. Moreover, the C-N atropisomers represent a fascinating and crucial chiral system, extensively found in natural products, pharmaceutical leads, and the frameworks of advanced materials. In this work, we have introduced a nickel-catalyzed regio- and enantioselective carbon-oxygen arylation reaction for atroposelective synthesis of N-arylisoquinoline-1,3(2H,4H)-diones. The high regioselectivity of C-O cleavage benefits from the high stability of the in situ formed (amido)ethenolate via oxidative addition. Additionally, the self-activation of the aryl C-O bond facilitates the reaction under mild conditions, leading to outstanding enantioselectivities. The diverse post-functionalizations of the axially chiral isoquinoline-1,3(2H,4H)-diones further highlighted the utility of this protocol in preparing valuable C-N atropisomers, including the chiral phosphine ligands.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:63 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 63(2024), 17 vom: 22. Apr., Seite e202402231 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Deng, Ruixian [VerfasserIn] |
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| Links: |
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| Themen: |
Asymmetric Catalysis |
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| Anmerkungen: |
Date Revised 15.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202402231 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM368974235 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2024 Wiley‐VCH GmbH. | ||
| 520 | |a The development of new methods for regio- and stereoselective activation of C-O bonds in ethers holds significant promise for synthetic chemistry, offering advantages in terms of environmental sustainability and economic efficiency. Moreover, the C-N atropisomers represent a fascinating and crucial chiral system, extensively found in natural products, pharmaceutical leads, and the frameworks of advanced materials. In this work, we have introduced a nickel-catalyzed regio- and enantioselective carbon-oxygen arylation reaction for atroposelective synthesis of N-arylisoquinoline-1,3(2H,4H)-diones. The high regioselectivity of C-O cleavage benefits from the high stability of the in situ formed (amido)ethenolate via oxidative addition. Additionally, the self-activation of the aryl C-O bond facilitates the reaction under mild conditions, leading to outstanding enantioselectivities. The diverse post-functionalizations of the axially chiral isoquinoline-1,3(2H,4H)-diones further highlighted the utility of this protocol in preparing valuable C-N atropisomers, including the chiral phosphine ligands | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Asymmetric Catalysis | |
| 650 | 4 | |a C−N Atropisomer | |
| 650 | 4 | |a C−O Bond Activation | |
| 650 | 4 | |a Nickel Catalysis | |
| 650 | 4 | |a Regioselective | |
| 700 | 1 | |a Dong, Puyang |e verfasserin |4 aut | |
| 700 | 1 | |a Ge, Jimeng |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Wenjing |e verfasserin |4 aut | |
| 700 | 1 | |a Xue, Xiaoping |e verfasserin |4 aut | |
| 700 | 1 | |a Duan, Longhui |e verfasserin |4 aut | |
| 700 | 1 | |a Shi, Linlin |e verfasserin |4 aut | |
| 700 | 1 | |a Gu, Zhenhua |e verfasserin |4 aut | |
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