Ni-Catalysed Intramolecular [4+4]-Cycloadditions of Bis-dienes towards Eight-membered Fused Bicyclic Systems: A Combined Experimental and Computational Study
| Autor: | Antonio Frontera, Héctor Fernández-Pérez, Antonio Bauzá, Anton Vidal-Ferran, Nuria Llorente |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Diene Double bond Bicyclic molecule 010405 organic chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Nickel chemistry Intramolecular force Yield (chemistry) |
| Zdroj: | RECERCAT (Dipòsit de la Recerca de Catalunya) Recercat. Dipósit de la Recerca de Catalunya instname |
| Popis: | Detailed investigations on the use of nickel(0)-based catalysts for intramolecular [4+4]-cycloadditions are presented. Nickel(0) complexes derived from electron-rich triarylphosphines proved to be efficient catalysts for intramolecular [4+4]- cycloadditions of an array of structurally diverse bis-dienes (10 examples, up to 78% isolated yield). The reported synthetic methodology leads to cis-eight-membered fused [6.3.0] bicyclic compounds as well as trans- or cis- eight-membered fused [6.4.0] bicyclic systems. Computational studies on the stereo-determining step of the reaction in combination with experimental results demonstrated that the stereochemical outcome is dictated by the length of the chain linking the two diene units and the geometry of the C=C double bonds of the substrates. |
| Databáze: | OpenAIRE |
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