Unveiling the Reactivity of Propargylic Hydroperoxides under Gold Catalysis.
Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the r...
| Publicado en: | Journal of the American Chemical Society Vol. 135; no. 2; pp. 898 - 906 |
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| Autores principales: | , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
1/16/2013
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| Sumario: | Controlled gold-catalyzed reactions of primary and secondary propargylic hydroperoxides with a variety of nucleophiles including alcohols, phenols, 2-hydroxynaphthalene-1,4-dione, and indoles allow the direct and efficient synthesis of β-functionalized ketones. Moreover, the utility of some of the resulting products for the selective preparation of fused polycycles has been demonstrated. In addition, density functional theory (DFT) calculations and O-labeling experiments were performed to obtain an insight into various aspects of the controlled reactivity of propargylic hydroperoxides with external nucleophiles under gold catalysis. |
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