Dual Lewis Acid/Photoredox-Catalyzed Addition of Ketyl Radicals to Vinylogous Carbonates in the Synthesis of 2,6-Dioxabicyclo[3.3.0]octan-3-ones
| Autor: | Maxwell D Gruber, Anne Marie Crooke, Nicholas J Foy, Katherine Forbes, Jeffrey S. Cannon |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Radical Organic Chemistry Diastereomer 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis Umpolung chemistry.chemical_compound Ketyl Yield (chemistry) Intramolecular force Lewis acids and bases Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 20(18) |
| ISSN: | 1523-7052 |
| Popis: | A combined Lewis acid/photoredox catalyst system enabled the intramolecular umpolung addition of ketyl radicals to vinylogous carbonates in the synthesis of 2,6-dioxabicyclo[3.3.0]octan-3-ones. This reaction proceeded on a variety of aromatic ketones to provide THF rings in good yield (up to 95%). Although diastereoselectivity was found to be modest (1.4–5:1) for the C-C bond forming reaction, the minor diastereomers were converted to 2,6-dioxabicyclo[3.3.0]octan-3-ones by an efficient Lewis acid-mediated epimerization cascade in up to 90% yield. |
| Databáze: | OpenAIRE |
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