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 regioselective O-annulation reactions. A wide range of oxygen-based heterocyclic scaffolds (21 examples) were achieved in excellent yield (up to 80%) and a detailed computation as well as deuterium-labelling investigations enabled all the plausible reaction pathways to be mapped and the rationalization of the recorded regioselectivity.

Site-selective Synthesis of 1,3-Dioxin-3-ones via a Gold(I) Catalyzed Cascade Reaction

Juzeng An
Methodology
;
Riccardo Pedrazzani
Methodology
;
Magda Monari
Conceptualization
;
Marco Bandini
Supervision
2020

Abstract

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 regioselective O-annulation reactions. A wide range of oxygen-based heterocyclic scaffolds (21 examples) were achieved in excellent yield (up to 80%) and a detailed computation as well as deuterium-labelling investigations enabled all the plausible reaction pathways to be mapped and the rationalization of the recorded regioselectivity.
Juzeng An, Riccardo Pedrazzani, Magda Monari, Marta Marin-Luna, Carlos Silva Lopez, Marco Bandini
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/768223
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