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Electrophilic olefin heterocyclization in organic synthesis. Stereoselective intramolecular amidomercuration of .GAMMA.-hydroxy-.DELTA.,.EPSILON.-unsaturated urethanes.
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1989
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Mercuric AcetateBioorganic ChemistryEngineeringBiochemistryNatural SciencesDiversity-oriented Synthesis.Epsilon.-unsaturated UrethanesCis-2-acetoxymercurymethyl-3-hydroxypyrrolidines 2AOrganic ChemistryStereoselective Intramolecular AmidomercurationStereoselective SynthesisChemistryε-Unsaturated Urethanes 1ASynthetic ChemistryBiomolecular EngineeringNatural Product Synthesis
Mercuric acetate driven cyclization of γ-hydroxy-δ, ε-unsaturated urethanes 1a, b proceeded regio- and stereoselectively to afford cis-2-acetoxymercurymethyl-3-hydroxypyrrolidines 2a, b, respectively. These were transformed into the key intermediates for several biologically active compounds.