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

Authors :
Mark E. Light
Ryan M Bennett
Wei Sun
David C. Harrowven
Dharyl C. Wilson
Source :
Chemical Communications. 57:5694-5697
Publication Year :
2021
Publisher :
Royal Society of Chemistry (RSC), 2021.

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.

Details

ISSN :
1364548X and 13597345
Volume :
57
Database :
OpenAIRE
Journal :
Chemical Communications
Accession number :
edsair.doi.dedup.....91a279ec584354c9656cf9778b16f6e9