Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes
| Autor: | Yoshinao Tamaru, Masanari Kimura |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Aldimine Grob fragmentation allyl cations catalysis Chemistry General Chemical Engineering Diol Trimethylenemethane Triethylborane General Chemistry palladium triethylborane Medicinal chemistry trimethylenemethane umpolung Umpolung allyl anions chemistry.chemical_compound Nucleophile Organic chemistry allyl alcohols |
| Zdroj: | Pure and Applied Chemistry. 80(5):979-991 |
| ISSN: | 0033-4545 |
| Popis: | Pd-Et3B catalytic system promotes the generation of allyl cations, allyl anions, and zwitterionic trimethylenemethane species from the corresponding allylic alcohols. Allyl cations react with a wide variety of nucleophiles, e.g., amines, active methylene compounds, 1,3,5-trihydroxybenzene, indoles, aldehydes (at the alpha;-position). The reaction is extended to dehydrative Grob fragmentation of 1,3-diols. Allyl anions react with aldimines to give homoallyl amines. Zwitterionic trimethylenemethane, generated from 2-mefhylene-1,3-propanediol, reacts with aldehydes and aldimines to provide 3-methylenecyclopentanols and 3-methylenepyrrolidines, respectively. Vinyl epoxide can be utilized as a synthetic equivalent of 3-butenyl 2-anion-1-cation. Pure and Applied Chemistry, 80(5), pp.979?991; 2008 |
| Databáze: | OpenAIRE |
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