Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels–Alder Reaction
| Autor: | Łukasz Albrecht, Joanna Dybowska, Maciej Saktura, Paulina Grzelak |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Letter Bicyclic molecule Double bond 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Cycloaddition 0104 chemical sciences Surface modification Physical and Theoretical Chemistry Inverse electron-demand Diels–Alder reaction Carbon |
| Zdroj: | Organic Letters |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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