Enantioselective Synthesis of 2,2-Disubstituted Tetrahydrofurans: Palladium-Catalyzed [3+2] Cycloadditions of Trimethylenemethane with Ketones
| Autor: | Barry M. Trost, Dustin A. Bringley |
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| Rok vydání: | 2013 |
| Předmět: |
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Molecular Trimethylenemethane chemistry.chemical_element Crystallography X-Ray Article Catalysis Stereocenter chemistry.chemical_compound Organometallic Compounds Organic chemistry Furans Phosphoramidite Molecular Structure Chemistry Aryl Enantioselective synthesis Stereoisomerism General Medicine General Chemistry Ketones Cycloaddition Cyclization Epimer Methane Palladium |
| Zdroj: | Angewandte Chemie International Edition. 52:4466-4469 |
| ISSN: | 1433-7851 |
| Popis: | An approach to 2,2-disubstituted 4-methylenetetrahydrofurans has been developed utilizing a cycloaddition of trimethylenemethane with aryl ketones, with formation of the products in up to 96% yield and 95% ee. The reaction is catalyzed by palladium in the presence of a phosphoramidite ligand possessing a stereogenic phosphorus, where only a single epimer at phosphorus yields the active catalyst. The identity of this epimer and the origin of its effect on reactivity are discussed. |
| Databáze: | OpenAIRE |
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