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Synlett 1998; 1998(1): 41-42
DOI: 10.1055/s-1998-1558
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The First Asymmetric Synthesis of (1R,1′S)-1-[1′-(Benzyloxycarbonyl-methylamino)-2′-phenylethyl]oxirane: a Promising Building Block for the Synthesis of Peptide Mimics

Christian Beier* , Ernst Schaumann, Gunadi Adiwidjaja
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany; Fax +49 (53 23) 72 28 58; E-mail: ernst.schaumann@tu-clausthal.de
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Publication Date:
31 December 2000 (online)

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The threo N-methyl oxirane 5 was prepared from (S)-N-methyl phenylalanine by bromoketone reduction or by epoxidation routes. The unexpected stereochemical result of the reduction of bromoketone 7 leading to the threo isomer is discussed.

amino epoxides - N-methyl amino acid - diastereoselective bromoketone reduction