180597-97-1Relevant academic research and scientific papers
An anomalous Dakin-West reaction of N-carbamate substituted prolines and trifluoroacetic anhydride
Kawase, Masami,Hirabayashi, Michitaka,Koiwai, Hiromi,Yamamoto, Katsumi,Miyamae, Hiroshi
, p. 641 - 642 (1998)
A novel transformation of N-alkoxycarbonylprolines 1 to 4-trifluoroacetyl-2,3-dihydropyrroles 2 was efficiently realized by utilizing trifluoroacetic anhydride, in which probable intermediates were mesoionic 1,3-oxazolium-5-olates B.
The Dakin-West reaction of N-alkoxycarbonyl-N-alkyl-α-amino acids employing trifluoroacetic anhydride
Kawase, Masami,Hirabayashi, Michitaka,Kumakura, Hiroko,Saito, Setsuo,Yamamoto, Katsumi
, p. 114 - 119 (2007/10/03)
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.
ENANTIOMERIC QUANTIFICATIONS OF AMINO ACIDS THROUGH THEIR Nα-ACYL AMIDES BY GAS CHROMATOGRAPHY.
Hosten, N.,Antenuis, M.J.O
, p. 48 - 50 (2007/10/02)
Apparent separation of 1.1 or higher on Chirasil Val III can be obtained for Nα-acyl N-alkyl aminoacid amides allowing the use of short capillary gas chromatographic columns.A clean derivatization protocol without racemization is described, proceding through the NCA derivatives that are prepared from "in situ" silylated amino acids with trimethylsilyl cyanide.
