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Synthesis 1996; 1996(6): 695-696
DOI: 10.1055/s-1996-4285
short paper
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Efficient Synthesis of (S)-Methyl Hexafluorovalinate

Reinhart Keese* , Christian Hinderling
  • *Institut für Organische Chemie, Universität Bern, Freiestrasse 3, CH-3012 Bern, Switzerland, Fax +31(631)3423; E-mail rk@ioc.unibe.ch
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Publikationsdatum:
31. Dezember 2000 (online)

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anti-Michael addition of (R)-(+)-1-phenylethylamine to methyl bis(trifluoromethyl)acrylate (1b) leads to a 52:48 mixture of the diastereomeric adducts (S,R)- and (R,R)-3a. After addition of hydrochloric acid, the diastereomeric salt (S,R)-3b crystallizes in a pure form to give, upon hydrogenolysis, an enantiomerically pure hydrochloric adduct of (+)-methyl hexafluorovalinate [(S)-4] to which the (S)-configuration was assigned. Treatment of (R,R)-3a with BBr3 gave hexafluorovaline [(R)-5].

β,β-trifluoromethyl acrylic acid - (R)-1-phenylethylamine - crystallisation - hexafluorovaline