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

Bennett, Ryan, Sun, Wei, Wilson, Dharyl Charles, Light, Mark and Harrowven, David C. (2021) A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans. ChemComm, 57 (46), 5694-5697. (doi:10.1039/D1CC02097H).

Record type: Article

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.

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Accepted/In Press date: 5 May 2021

e-pub ahead of print date: 5 May 2021

Published date: 11 June 2021

Additional Information: Funding Information: We gratefully acknowledge financial support from the European Regional Development Fund [ERDF Interreg Va programme (Project 121)] and EPSRC [EP/P013341/1, EP/L003325/1 and EP/K039466/1]. Publisher Copyright: © The Royal Society of Chemistry 2021.

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