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Synthesis 1985; 1985(9): 850-855
DOI: 10.1055/s-1985-31363
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Diastereo- and Enantioselective Synthesis of Fluorinated Threonines

Carlo Scolastico* , Esterino Conca, Laura Prati, Giuseppe Guanti, Luca Banfi, Adriano Berti, Paolo Farina, Umberto Valcavi
  • *Istituto di Chimica Organica dell'Università via Venezian 21, I-20133 Milano, Italy
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Publikationsdatum:
27. September 2002 (online)

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(d,l)-threo and allo-2-amino-4,4,4-trifluoro-3-hydroxybutanoic acids are synthesised from ethyl trifluoroacetoacetate via reduction and saponification of the 4,4,4-trifluoro-3-hydroxy-2-methoxyiminobutanoate. threo-Isomers are stereospecifically obtained by epimerisation of allo-isomers via the corresponding oxazolidinones. An acylation and stereoselective reduction sequence performed on ethyl N,N-dibenzylaminoacetate also leads to threo-isomers (1A) in good yields. An enantioselective synthesis of (L)-4-fluorothreonine by regiospecific opening of (2S), (3R)-3-benzyloxyoxiranecarboxylic acid is reported.

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