Remote Asymmetric Oxa-Diels-Alder Reaction of 5-Allylic Furfurals via Dearomatizative Tetraenamine Catalysis.
Xiao-Long HeHui-Ru ZhaoChuan-Qi DuanWei DuYing-Chun ChenPublished in: Organic letters (2018)
A previously unreported activation mode is developed through the generation of dearomatizative tetraenamine species between 5-allylic furfurals and a bifunctional amine-thiourea catalyst. The very remote ζ,η-alkenes perform as effective HOMO-raised dienophiles in inverse-electron-demand oxa-Diels-Alder cycloadditions with isatin-derived oxadiene substrates, delivering multifunctional spirocyclic oxindoles incorporating a dihydropyran skeleton in moderate to high yields with good to excellent enantio- and diastereoselectivity.
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