| Literature DB >> 10705486 |
M Kawase1, M Hirabayashi, H Kumakura, S Saito, K Yamamoto.
Abstract
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 good yields.Entities:
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Year: 2000 PMID： 10705486 DOI： 10.1248/cpb.48.114
Source DB: PubMed Journal: Chem Pharm Bull (Tokyo) ISSN： 0009-2363 Impact factor: 1.645