Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water
A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:22 |
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| Enthalten in: |
Organic letters - 22(2020), 11 vom: 05. Juni, Seite 4306-4310 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
He, Xinwei [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 23.09.2020 Date Revised 23.09.2020 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.0c01357 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM310233488 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Xie, Mengqing |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Ruxue |e verfasserin |4 aut | |
| 700 | 1 | |a Choy, Pui Ying |e verfasserin |4 aut | |
| 700 | 1 | |a Tang, Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Shang, Yongjia |e verfasserin |4 aut | |
| 700 | 1 | |a Kwong, Fuk Yee |e verfasserin |4 aut | |
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