Synthesis of 2-Pyrrolidinones by Palladium-Catalyzed [3+2] Cycloaddition of Isocyanates
| Autor: | Thomas Schlatzer, Rolf Breinbauer, Marko Kljajic |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Alkene Organic Chemistry Trimethylenemethane 010402 general chemistry 01 natural sciences Medicinal chemistry Isocyanate Cycloaddition 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Nucleophile Electrophile Pyrrolidinones |
| Zdroj: | Synlett. 30:581-585 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0037-1610692 |
| Popis: | Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated 2-pyrrolidinones occurs without olefin isomerization and without epimerization of the stereogenic centers. Mechanistic investigations suggest an initial N-allylation of the isocyanate followed by nucleophilic ring closure furnishing the desired 2-pyrrolidinones. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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