Synthetic Versatility of<i>N</i>-(Silylmethyl)imines: Water-Induced Generation of<i>N</i>-Protonated Azomethine Ylides of Nonstabilized Type and Fluoride-Induced Generation of 2-Azaallyl Anions
N-(Silylmethyl)imines generateN-protonatedazomethineylides of nonstabilized type when treated with water in HMPA, which undergo stereospecific and regioselectivecycloadditions with electron-poo...
Trifluoromethyl-substituted Δ3-imidazolines: Synthesis and reactivity
作者:Christopher W. Derstine、David N. Smith、John A. Katzenellenbogen
DOI:10.1016/s0040-4039(97)00934-9
日期:1997.6
We describe the preparation of various 4-trifluoromethyl-substituted Delta(3)-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from alpha-silylimines and trifluoroacetonitrile by a 3+2 cycloaddition, and they can be hydrolyzed in weak acid to trifluoromethyl ketones. Additionally, we have identified several ring-opened compounds which result from treatment of the imidazolines with acid or base. Attempts to alkylate the imidazolines led to ring-opened products, so that the alkylation sequence ultimately produced N-alkylated amino acid-derived trifluoromethyl ketones. (C) 1997 Elsevier Science Ltd.
Hullot,P.; Cuvigny,T., Bulletin de la Societe Chimique de France, 1973, p. 2989 - 2992