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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| http://dx.doi.org/10.1021/acs.orglett.7b03942 | DOI Listing |
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Remote Asymmetric Oxa-Diels-Alder Reaction of 5-Allylic Furfurals via Dearomatizative Tetraenamine Catalysis.
Org Lett
February 2018
Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
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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