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Synlett 1995; 1995(11): 1159-1160
DOI: 10.1055/s-1995-5201
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Cyclization of a Chiral N-Crotyl Methoxycarbonylacetamide Mediated by Mn(III). An Easy Entry to (R)-3-Pyrrolidineacetic Acid

Barbara Cardillo, Roberta Galeazzi, Giovanna Mobbili, Mario Orena*
  • *Dipartimento di Scienze dei Materiali e della Terra, Università di Ancona - Via Brecce Bianche - 60131 Ancona, Italy
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Publication Date:
31 December 2000 (online)

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The N-crotyl methoxycarbonylacetamide 3, containing (S)-phenylethylamine as the chiral auxiliary, was cyclised with Mn(III), to give an easily separable mixture of diastereomeric pyrrolidin-2-ones in 70:30 d.r. The major isomer is a key intermediate to (R)-3-pyrrolidineacetic acid, inhibitor of GABA uptake in astrocytes.

cyclization - chiral auxiliary - (S)-phenylethylamine - amino acids