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Synthesis 1995; 1995(10): 1223-1224
DOI: 10.1055/s-1995-4080
short paper
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Synthesis of Enantiopure (S)-α-Hydroxy Carboxanilides from (S)-α-Amino Acids

Ulrich Girreser* , Christian R. Noe
  • *Institut für Pharmazeutische Chemie der Johann-Wolfgang-Goethe Universität, Christian Doppler Laboratorium für Chemie chiraler Verbindungen, Marie-Curie-Str. 9, D-60439 Frankfurt, Germany, Fax +49(69)79829352
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Publication Date:
31 December 2000 (online)

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α-Hydroxy carboxanilides 3a-c were obtained without racemization in a synthetically simple way starting from the corresponding α-amino acids by diazotization and subsequent treatment of the sodium α-hydroxy carboxylates with anilinium chloride in moderate yields. The enantiopurity of 3a-c was easily determined by 1H NMR spectroscopy of the diastereomeric O,O-acetals 5/6a-c derived from exo-lactol 4.

Synthesis of enantiopure (S)-α-hydroxy-carboxanilides from (S)-α-amino acids