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Synthesis 1996; 1996(7): 833-837
DOI: 10.1055/s-1996-4299
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Asymmetric Synthesis; XXXVII: Synthesis of 2,6-Disubstituted Piperazines from Chiral Non-Racemic Lactams

Vincent Schanen, Marie-Pierre Cherrier, Sebastião Jose de Melo, Jean-Charles Quirion* , Henri-Philippe Husson
  • *Laboratoire de Chimie Thérapeutique associé au CNRS, Faculté des Sciences Pharmaceutiques et Biologiques, Université R. Descartes, 4, Avenue de l’Observatoire, F-75270 Paris Cedex 06, France, Fax +33(1)43291403
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Publication Date:
31 December 2000 (online)

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General and convenient syntheses of optically active 2,6-disubstituted piperazines are described. The method is based on diastereoselective alkylation of lactam 8 derived from (R)-(-)-phenylglycinol followed by a regio- and diastereoselective functionalisation of carbamates 10c and 10d. This procedure allowed the preparation of new α-amino acids 15 and 16.

asymmetric synthesis - (R)-(-)-phenylglycinol - 2,6-disubstituted piperazine - metalation of carbamate - α-amino acid