Site-selective synthesis of 1,3-dioxin-3-ones via a gold(i) catalyzed cascade reaction
A novel gold(i)-catalyzed protocol for the synthesis of 4H-1,3-dioxin-3-ones is presented. The protocol exploits a metal induced cascade sequence involving a [3,3]-sigmatropic rearrangement followed by regioselectiveO-annulation reactions. A wide range of oxygen-based heterocyclic scaffolds (21 exam...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (56), p.7734-7737 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | An, Juzeng Pedrazzani, Riccardo Monari, Magda Marin-Luna, Marta Silva Lopez, Carlos Bandini, Marco |
| description | A novel gold(i)-catalyzed protocol for the synthesis of 4H-1,3-dioxin-3-ones is presented. The protocol exploits a metal induced cascade sequence involving a [3,3]-sigmatropic rearrangement followed by regioselectiveO-annulation reactions. A wide range of oxygen-based heterocyclic scaffolds (21 examples) were achieved in excellent yield (up to 80%) and a detailed computational investigation as well as deuterium-labelling investigations enabled all the plausible reaction pathways to be mapped and the rationalization of the recorded regioselectivity. |
| doi_str_mv | 10.1039/d0cc02703k |
| format | Article |
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| subjects | Cartesian coordinates Cascade chemical reactions Chemical reactions Chemical synthesis Chemistry Chemistry, Multidisciplinary Crystallography Deuterium Dioxins Gold NMR Nuclear magnetic resonance Physical Sciences Regioselectivity Science & Technology |
| title | Site-selective synthesis of 1,3-dioxin-3-ones via a gold(i) catalyzed cascade reaction |
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