139657-82-2Relevant academic research and scientific papers
Preparation and Reactions of Ethyl (R,R)- and (S,S)-3-Trifluoromethyloxirane-2-carboxylate, a Versatile, Easily Accessible CF3-Containing Building Block for Synthesis
Bussche-Huennefeld, Christoph von .,Seebach Dieter
, p. 1273 - 1282 (2007/10/02)
A facile three-step route has been elaborated leading from 4,4,4-trifluoro-3-oxobutanoate to the trifluoro glycidic ester 1 mentioned in the title (0.1-mole scale).Reactions with azide (--> 4, 5) and with organometallic compounds such as cuprates (--> 3, 6), lithium (--> 7, 8), and magnsium derivatives (--> 9-11) furnish novel enantiomerically pure trifluoromethyl-substituted carboxylic esters, ketones, diols, and epoxy alcohols.The latter ones undergo selective isomerizations by Payne rearrangement (11 --> 12) in aqueous NaOH/acetone or tert-butyl alcohol. Key Words: Glycidic esters / Oxiranecarboxylic esters / Threonine / allo-Threonine / Epoxy alcohols / Flustrates / Payne rearrangement
