ol0c00619_si_001.pdf (7.11 MB)
Synthesis of Tetrasubstituted Furans through One-Pot Formal [3 + 2] Cycloaddition Utilizing [1,2]-Phospha-Brook Rearrangement
journal contribution
posted on 2020-02-25, 15:36 authored by Azusa Kondoh, Kohei Aita, Sho Ishikawa, Masahiro TeradaAn
efficient method for the synthesis of tetrasubstituted furans was
developed by utilizing the [1,2]-phospha-Brook rearrangement under
Brønsted base catalysis. The two-step one-pot formal [3 + 2]
cycloaddition involves the nucleophilic addition of a propargyl anion,
which is catalytically generated through the [1,2]-phospha-Brook rearrangement,
to an aldehyde and the subsequent intramolecular cyclization mediated
by N-iodosuccinimide to provide 2,4,5-trisubstituted-3-iodofurans.
The present method with readily available substrates provides new
access to a wide range of well-organized tetrasubstituted furans.
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Phospha-BrookBr ønsted base catalysistetrasubstituted furansTetrasubstitutediodosuccinimideUtilizingcycloadditioncyclizationaccessFuranpropargylmethodtrisubstitutedsynthesisphospha-Brookone-pot-3-iodofuranintramolecularRearrangementsubstratecatalyticallynucleophilicanionaldehydeFormalrearrangementOne-PotSynthesiCycloaddition
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