Stereoselective Double Spirocyclization of 2‑Benzyl-3-alkynyl Chromone with Nitrone via Gold-Catalyzed Cascade Reactions
A novel, highly stereoselective gold-catalyzed spirocyclization of 2-benzyl-3-alkynyl chromone with nitrone is described. This cascade reaction involves gold-catalyzed cycloisomerization, nitrone-olefin [3 + 2]-annulation, alkene oxidation, and rearrangement for the formation of spirocyclic products...
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| Veröffentlicht in: | Organic letters 2024-08, Vol.26 (31), p.6675-6680 |
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| container_title | Organic letters |
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| creator | Sasane, Amit Vijay Chiou, Chun-Tang Chang, Ming-Yiang Li, Wen-Tai |
| description | A novel, highly stereoselective gold-catalyzed spirocyclization of 2-benzyl-3-alkynyl chromone with nitrone is described. This cascade reaction involves gold-catalyzed cycloisomerization, nitrone-olefin [3 + 2]-annulation, alkene oxidation, and rearrangement for the formation of spirocyclic products. Interestingly, the isoxazolidine ring generated from [3 + 2]-annulation donates oxygen to alkene to generate a new pyran-3(4H)-one and azetidine ring for dispiro-benzofuran formation upon heating. This work demonstrates the one-pot, gold-catalyzed, multiple-step reaction, and the reaction temperature directly affects the formation of spirocyclic products. |
| doi_str_mv | 10.1021/acs.orglett.4c02338 |
| format | Article |
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| title | Stereoselective Double Spirocyclization of 2‑Benzyl-3-alkynyl Chromone with Nitrone via Gold-Catalyzed Cascade Reactions |
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