Issue 56, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
14 apr 2020
Accepted
17 jún 2020
First published
17 jún 2020

Chem. Commun., 2020,56, 7734-7737

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, 56, 7734 DOI: 10.1039/D0CC02703K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements