The Dakin-West Reaction of N-Alkoxycarbonyl-N-alkyl-α-amino Acids Employing Trifluoroacetic Anhydride

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概要

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• 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 NaBH_4 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.

• 公益社団法人日本薬学会の論文
• 2000-01-01

著者

• Saito Setsuo

  Faculty of Pharmaceutical Science,Josai University

• KAWASE Masami

  Faculty of Pharmaceutical Sciences, Josai University

• Kawase Masami

  Faculty Of Pharmaceutical Sciences Josai University

• Saito Setsuo

  Faculty Of Pharmaceutical Sciences Josai University

• YAMAMOTO Katsumi

  Faculty of Pharmaceutical Sciences, Josai University

• HIRABAYASHI Michitaka

  Faculty of Pharmaceutical Sciences, Josai University

• KUMAKURA Hiroko

  Faculty of Pharmaceutical Sciences, Josai University

• Kumakura Hiroko

  Faculty Of Pharmaceutical Sciences Josai University

• Hirabayashi Michitaka

  Faculty Of Pharmaceutical Sciences Josai University

• Yamamoto Katsumi

  Faculty Of Pharmaceutical Sciences Josai University

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