Chemical and Pharmaceutical Bulletin p. 114 - 119 (2000)
Update date:2022-07-30
Topics:
Kawase, Masami
Hirabayashi, Michitaka
Kumakura, Hiroko
Saito, Setsuo
Yamamoto, Katsumi
The Dakin-West reaction of N-alkoxycarbonyl-N-alkyl-α-amino acids (1a - j) with trifluoroacetic anhydride in the presence of pyridine gave α-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 good yields.
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