A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans.
Ryan M BennettWei SunDharyl C WilsonMark E LightDavid C HarrowvenPublished in: Chemical communications (Cambridge, England) (2021)
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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