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Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
[Image: see text] In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the...
| Autores principales: | , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2020
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497662/ https://www.ncbi.nlm.nih.gov/pubmed/32065757 http://dx.doi.org/10.1021/acs.orglett.0c00138 |
| Sumario: | [Image: see text] In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the formation of biologically relevant [2.2.2]-bicyclic lactones. Their functionalization potential has been confirmed in selected, diastereoselective transformations. |
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