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: | Foy NJ; Department of Chemistry , Occidental College , Los Angeles , California 90041 , United States., Forbes KC; Department of Chemistry , Occidental College , Los Angeles , California 90041 , United States., Crooke AM; Department of Chemistry , Occidental College , Los Angeles , California 90041 , United States., Gruber MD; Department of Chemistry , Occidental College , Los Angeles , California 90041 , United States., Cannon JS; Department of Chemistry , Occidental College , Los Angeles , California 90041 , United States. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2018 Sep 21; Vol. 20 (18), pp. 5727-5731. Date of Electronic Publication: 2018 Sep 06. |
| DOI: | 10.1021/acs.orglett.8b02442 |
| Abstrakt: | 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: | MEDLINE |
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