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A Versatile Synthesis of 3-Phenylsulfonylpyrroles from α-Amino Acids
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1995
Year
Chemical EngineeringM-cpba Oxidationα-Benzamidoalkyl Ketones 4A-eEngineeringNatural SciencesDiversity-oriented SynthesisOrganic ChemistryDiborane ReductionStereoselective SynthesisChemistryHeterocycle ChemistrySynthetic ChemistryBiomolecular Engineeringα-Amino Acids
Reaction between α-benzamidoalkyl ketones 4a-e and the vinyl phosphonium salt 1 produces 3-phenylthio-3-pyrrolines 5a-e which can be converted into N-benzyl-3-phenylsulfonyl pyrroles 7a-e by m-CPBA oxidation, diborane reduction and DDQ aromatisation.