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Synthesis 1995; 1995(9): 1151-1154
DOI: 10.1055/s-1995-4068
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A Versatile Synthesis of 3-Phenylsulfonylpyrroles from α-Amino Acids

Ian Burley, Alan T. Hewson*
  • *Division of Chemistry and Health Research Institute, Sheffield Hallam University, Pond Street, Sheffield S1 1WB, England, Fax +44(114)2533085
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Publication Date:
31 December 2000 (online)

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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.

pyrrole - phenylsulfonyl - intramolecular Wittig reaction - aromatisation

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