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Synlett 1994; 1994(5): 345-346
DOI: 10.1055/s-1994-22848
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One-step Reduction-Wittig Olefination of Methyl Pyroglutamate: Chiral Syntheses of (5S)-5-Alkenyl-2-pyrrolidinones and (S)-Vigabatrin®

Z. Y. Wei* , E. E. Knaus
  • *Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta T6G 2N8, Canada
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Publication Date:
22 March 2002 (online)

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An efficient methodology for the enantioselective synthesis of (5S)-5-alkenyl-2-pyrrolidinones was developed. The title chiral compounds were prepared starting from (5S)-methyl 1-t-butoxycarbonylpyroglutamate using three tandem reduction-Wittig olefination-oxidation reactions in 32-52% yield.