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Synlett 1995; 1995(7): 753-754
DOI: 10.1055/s-1995-5068
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Asymmetric Reduction of 2-(N-Arylimino)-3,3,3-trifluoropropanoic Acid Esters Leading to Chiral 3,3,3-Trifluoroalanine and Its Derivatives

Takashi Sakai, Fengyang Yan, Kenji Uneyama*
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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(R)-3,3,3-Trifluoroalanine and its derivatives have been synthesized enantioselectively by the asymmetric reduction of 2-(N-arylimino)-3,3,3-trifluoropropanoic acid esters with (S)-oxazaborolidine-catecholborane system. The absolute configuration was determined to be R by X-Ray crystallographic analysis of the corresponding N-(S)-(+)-camphorsulfonyl derivative.

asymmetric reduction - imino ester - catecholborane - oxazaborolidine - 3,3,3-trifluoroalanine