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Synthesis of New δ-(Polyfluoroalkyl)-δ-hydroxy-α-amino Acids

✍ Scribed by Nataliya A. Tolmacheva; Igor I. Gerus; Violetta G. Dolovanyuk; Ivan S. Kondratov; Günter Haufe

Publisher: John Wiley and Sons
Year: 2009
Tongue: English
Weight: 227 KB
Volume: 2009
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200900684

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✦ Synopsis

Abstract

New δ‐(polyfluoroalkyl)‐δ‐hydroxy‐α‐amino acids were synthesized from the corresponding starting 3‐(benzoylamino)‐6‐(polyfluoroalkyl)‐2__H__‐pyran‐2‐ones. The key step of the synthesis was the hydrogenation of the pyrone ring. Stereoselectivity and yields depended dramatically on the reaction conditions and the nature of the polyfluoroalkyl group. Various conditions were used for the preparation of both mixtures of diastereomers and pure diastereomers of the target amino acids. The obtained δ‐(polyfluoroalkyl)‐δ‐hydroxy‐α‐amino acids are of interest as analogues of 2‐amino‐5‐hydroxyvaleric acid and glutamic acid.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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