Chemistry Letters · 2003 · 30 citations · 21 references
Natural SciencesChemistryOrganic ChemistryOrganometallic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisOrganic SynthesisDouble Bond ConfigurationRing-forming ReactionsSuccessive Substitution
Abstract 1,1-Disubstituted and trisubstituted alkenes were converted into the corresponding β,γ-unsaturated amines 4 via three steps: the initial formation of α,β-unsaturated diphenylsulfonium triflates 2 from alkenes and diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1), followed by double bond migration of 2 to β,γ-unsaturated sulfonium triflates 3 with primary or secondary amines, and successive nucleophilic substitution of 3 with these amines.
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Shin-ichi INOUE, Hidemasa Takaya, Kazuhide Tani et al. · Journal of the American Chemical Society · 1990 · 171 citations