Rhodium-Catalyzed Diastereoselective C-H Activation/[4 + 2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes
Herein, we report a rare example of rhodium-catalyzed C-H activation/[4 + 2] annulation of alkenyl amides with bicyclic alkenes under mild and green conditions. The reactivity of the rhodium catalyst in this study differed from that observed in cobalt-catalyzed C-H activation/[3 + 2] annulation between vinylic amides and bicyclic alkenes. In addition, the reaction was performed in EtOH at room temperature, which also displayed excellent diastereoselectivity, good functional group tolerance, and air compatibility. A series of novel bridged-ring skeletons were obtained in good to excellent yields. Scale-up experiments were carried out with 1 or 0.75 mol % rhodium catalyst, affording the desired bridged-ring skeleton in excellent yields.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Organic letters - 26(2024), 2 vom: 19. Jan., Seite 483-487 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Wang, Yan [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Revised 19.01.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.orglett.3c03819 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM366883321 |
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| 520 | |a Herein, we report a rare example of rhodium-catalyzed C-H activation/[4 + 2] annulation of alkenyl amides with bicyclic alkenes under mild and green conditions. The reactivity of the rhodium catalyst in this study differed from that observed in cobalt-catalyzed C-H activation/[3 + 2] annulation between vinylic amides and bicyclic alkenes. In addition, the reaction was performed in EtOH at room temperature, which also displayed excellent diastereoselectivity, good functional group tolerance, and air compatibility. A series of novel bridged-ring skeletons were obtained in good to excellent yields. Scale-up experiments were carried out with 1 or 0.75 mol % rhodium catalyst, affording the desired bridged-ring skeleton in excellent yields | ||
| 650 | 4 | |a Journal Article | |
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| 700 | 1 | |a Zhang, Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Nian, Yong |e verfasserin |4 aut | |
| 700 | 1 | |a Wu, Xiaowei |e verfasserin |4 aut | |
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