Synthesis of Trifluoromethylated Isoxazolidines: 1,3-Dipolar Cycloaddition of Nitrosoarenes, (Trifluoromethyl)diazomethane, and Alkenes
| Autor: | Livia N. Cavalcanti, Gary A. Molander |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Trifluoromethyl
Cycloaddition Reaction Hydrocarbons Fluorinated Molecular Structure Nitroso Compounds Diazomethane Organic Chemistry Alkenes Biochemistry Article Catalysis Cycloaddition chemistry.chemical_compound chemistry Reagent 1 3-Dipolar cycloaddition Organic chemistry Indicators and Reagents Physical and Theoretical Chemistry Oxazoles |
| Zdroj: | Organic Letters. 15:3166-3169 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol401402d |
| Popis: | Isoxazolidines have proven to be important substrates in synthetic organic chemistry. Limited examples in the literature that provide trifluoromethylated versions of these compounds have prompted us to investigate a 1,3-dipolar cycloaddition route providing access to N-functionalized isoxazolidines containing a trifluoromethyl group. Thus, a 1,3-dipolar cycloaddition of nitrosoarenes, (trifluoromethyl)diazomethane, and alkenes was developed. The starting materials can be synthesized from easy to handle and accessible reagents. The reaction proved to be tolerant of a variety of electron-deficient alkenes and nitrosoarenes. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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