Issue 29, 2021

A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan

Abstract

A silver-catalyzed diastereoselective one-pot domino cyclization-migration/inverse electron-demand oxo-Diels–Alder reaction has been disclosed in this communication through the in situ generated cyclobutane-fused furan intermediate with 4-vinyl-2,3-dioxopyrrolidine for the construction of 2-oxopyrrolidine-fused tricyclic compounds in moderate to good yields with a broad substrate scope under mild conditions. This new synthetic protocol features good efficiency and atom- and step-economy. A plausible reaction mechanism has also been proposed on the basis of previous reports, NMR tracing and control experiments.

Graphical abstract: A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan

Supplementary files

Article information

Article type
Communication
Submitted
06 Feb 2021
Accepted
06 Mar 2021
First published
08 Mar 2021

Chem. Commun., 2021,57, 3599-3602

A silver-catalyzed domino inverse electron-demand oxo-Diels–Alder reaction of 3-cyclopropylideneprop-2-en-1-ones with 2,3-dioxopyrrolidines via cyclobutane-fused furan

Y. Zhang, Y. Wei and M. Shi, Chem. Commun., 2021, 57, 3599 DOI: 10.1039/D1CC00707F

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