Issue 46, 2021
From the journal:

Chemical Communications

A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans†

Ryan M. Bennett,a   Wei Sun,a   Dharyl C. Wilson,a   Mark E. Lighta  and  David C. Harrowven ORCID logo *a  

* Corresponding authors

a Chemistry, University of Southampton, Highfield, Southampton, UK
E-mail: dch2@soton.ac.uk

Abstract

A dichotomy between the additions of organolithiums and lithium amides to cyclobutenediones is described wherein the former give carbonyl addition products while the latter induce ring opening by enone cleavage via O- to C-lithium transfer. This distinct mode of ring scission gives access to 2-oxobut-3-enamides and tetrasubstituted furans.

Graphical abstract: A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans

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Article information

DOI
https://doi.org/10.1039/D1CC02097H
Article type
Communication
Submitted
20 Apr 2021
Accepted
05 May 2021
First published
05 May 2021
This article is Open Access
Creative Commons BY license

Chem. Commun., 2021,57, 5694-5697

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A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans

R. M. Bennett, W. Sun, D. C. Wilson, M. E. Light and D. C. Harrowven, Chem. Commun., 2021, 57, 5694 DOI: 10.1039/D1CC02097H

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