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Site-selective synthesis of 1,3-dioxin-3-ones via a gold(i) catalyzed cascade reaction

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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 computational investigation as well as deuterium-labelling investigations enabled all the plausible reaction pathways to be mapped and the rationalization of the recorded regioselectivity.

Graphical abstract: Site-selective synthesis of 1,3-dioxin-3-ones via a gold(i) catalyzed cascade reaction

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Supplementary files

Article information


Submitted
14 Apr 2020
Accepted
17 Jun 2020
First published
17 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Site-selective synthesis of 1,3-dioxin-3-ones via a gold(I) catalyzed cascade reaction

J. An, R. Pedrazzani, M. Monari, M. Marin-Luna, C. S. Lopez and M. Bandini, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02703K

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