Hydrated [3+2] Cyclotelomerization of Butafulvenes to Create Multiple Contiguous Fully Substituted Carbon Centers
© 2023 Wiley-VCH GmbH..
The construction of multiple continuous fully substituted carbon centers, which serve as unique structural motif in natural products, is a challenging topic in organic synthesis. Herein, we report a hydrated [3+2] cyclotelomerization of butafulvenes to create contiguous fully substituted carbon backbone. In the presence of scandium triflate, all-carbon skeleton with spiro fused tricyclic ring can be constructed in high diastereoselectivity by utilizing butafulvene as the synthon. Mechanistic studies suggest that this atom-economic reaction probably proceeds through a synergistic process containing butafulvenes dimerization and nucleophilic attack by water. In addition, the tricyclic product can undergo a series of synthetic derivatizations, which highlights the potential applications of this strategy. The recyclability of Sc(OTf)3 has also been demonstrated to show its robust performance in this hydrated cyclotelomerization.
| 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), 6 vom: 05. Feb., Seite e202317299 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhou, Bo-Chao [VerfasserIn] |
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| Links: |
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| Themen: |
Butafulvene |
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| Anmerkungen: |
Date Revised 01.02.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202317299 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a The construction of multiple continuous fully substituted carbon centers, which serve as unique structural motif in natural products, is a challenging topic in organic synthesis. Herein, we report a hydrated [3+2] cyclotelomerization of butafulvenes to create contiguous fully substituted carbon backbone. In the presence of scandium triflate, all-carbon skeleton with spiro fused tricyclic ring can be constructed in high diastereoselectivity by utilizing butafulvene as the synthon. Mechanistic studies suggest that this atom-economic reaction probably proceeds through a synergistic process containing butafulvenes dimerization and nucleophilic attack by water. In addition, the tricyclic product can undergo a series of synthetic derivatizations, which highlights the potential applications of this strategy. The recyclability of Sc(OTf)3 has also been demonstrated to show its robust performance in this hydrated cyclotelomerization | ||
| 650 | 4 | |a Journal Article | |
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| 650 | 4 | |a Cyclotelomerization | |
| 650 | 4 | |a Fully Substituted Carbon | |
| 650 | 4 | |a Hydration | |
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| 700 | 1 | |a Song, Ting-Ting |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Yang |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Li-Ming |e verfasserin |4 aut | |
| 700 | 1 | |a Ji, Ding-Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Wan, Boshun |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Qing-An |e verfasserin |4 aut | |
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