Christoph-Sweder Eberhard Wilhelm von dem Bussche-Hünnefeld, D. Seebach
May 1, 1992
Citations
0
Influential Citations
31
Citations
Journal
Chemische Berichte
Abstract
Preparation and Reactions of Ethyl (R,R)- and (S,S)-3-Trifluoromethyloxirane-2-carboxylate, a Versatile, Easily Accessible CF3-Containing Building Block for Synthesis 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 magnesium 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.