Synthesis of Spirotetrahydrofuran Oxindoles via Palladium-Catalyzed [4 + 1] Cycloaddition of Diphenyl 2-Oxoindolin-3-yl Phosphates and 2-Methylidenetrimethylene Carbonate
A novel palladium-catalyzed [4 + 1] cycloaddition to give spirotetrahydrofuran oxindoles has been developed, in which diphenyl 2-oxoindolin-3-yl phosphates were used as the both electrophilic and nucleophilic C1 synthons at C-3 of the oxindole unit and 2-methylidenetrimethylene carbonate was used as the 1,4-dipole. The cycloannulation was performed at room temperature and provided the corresponding spirotetrahydrofuran oxindoles in good to excellent yields. The present method affords a new strategy for the construction of spirooxindole derivatives with unique three-dimensional structures.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
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| Enthalten in: |
Organic letters - 23(2021), 16 vom: 20. Aug., Seite 6499-6503 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Yuming [VerfasserIn] |
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| Anmerkungen: |
Date Revised 20.08.2021 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.1c02306 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM328869554 |
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| 100 | 1 | |a Li, Yuming |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of Spirotetrahydrofuran Oxindoles via Palladium-Catalyzed [4 + 1] Cycloaddition of Diphenyl 2-Oxoindolin-3-yl Phosphates and 2-Methylidenetrimethylene Carbonate |
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| 500 | |a Date Revised 20.08.2021 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a A novel palladium-catalyzed [4 + 1] cycloaddition to give spirotetrahydrofuran oxindoles has been developed, in which diphenyl 2-oxoindolin-3-yl phosphates were used as the both electrophilic and nucleophilic C1 synthons at C-3 of the oxindole unit and 2-methylidenetrimethylene carbonate was used as the 1,4-dipole. The cycloannulation was performed at room temperature and provided the corresponding spirotetrahydrofuran oxindoles in good to excellent yields. The present method affords a new strategy for the construction of spirooxindole derivatives with unique three-dimensional structures | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Jie, Jiyang |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Hongyun |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Haijun |e verfasserin |4 aut | |
| 700 | 1 | |a Fu, Hua |e verfasserin |4 aut | |
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