The Dakin-West reaction of N-alkoxycarbonyl-N-alkyl-alpha-amino acids employing trifluoroacetic anhydride.

@article{Kawase2000TheDR,
  title={The Dakin-West reaction of N-alkoxycarbonyl-N-alkyl-alpha-amino acids employing trifluoroacetic anhydride.},
  author={M. Kawase and Masumi Hirabayashi and Hideko Kumakura and Setsuo Saito and Keiji Yamamoto},
  journal={Chemical & pharmaceutical bulletin},
  year={2000},
  volume={48 1},
  pages={114-9}
}
The Dakin-West reaction of N-alkoxycarbonyl-N-alkyl-alpha-amino acids (1a-j) with trifluoroacetic anhydride in the presence of pyridine gave alpha-amido trifluoromethyl ketones (2a-j), in which probable intermediates were mesoionic 1,3-oxazolium-5-olates (munchnones). The diastereoselective reduction of 2a-f with NaBH4 gave the threo-aminoalcohols (5a-f), which may be explained by the Felkin-Anh model. This was confirmed by converting 5a-f into trans-5-trifluoromethyl-2-oxazolidinones (6a-f) in… CONTINUE READING