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Synthetic Studies on Echinulin and Related Natural Products. I. : Acid-Catalyzed Amino-Claisen Rearrangement of N-Allylaniline and N, N-Diallylaniline Derivatives
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1977
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Enantioselective SynthesisEngineeringBiochemistryN-diallylaniline DerivativesSynthetic StudiesRelated AlkaloidsTotal SynthesisOrganic ChemistryNatural Product BiosynthesisStereoselective SynthesisBoron Trifluoride EtheratePharmacologyAsymmetric CatalysisSynthetic ChemistryBiomolecular EngineeringRelated Natural ProductsNatural Product Synthesis
In connection with a total synthesis of echinulin and related alkaloids, acid-catalyzed amino-Claisen rearrangement of N-allylaniline (2), N, 2-diallylaniline (4), N, 2, 6-trially-laniline (7), and N, N-diallylaniline (5) was examined in refluxing xylene, in the presence of zinc chloride or boron trifluoride etherate. Boron trifluoride etherate was found to be more effective acid for this rearrangement.