TY - JOUR
T1 - Trifluoromethyl-substituted Δ3-imidazolines
T2 - Synthesis and reactivity
AU - Derstine, Christopher W.
AU - Smith, David N.
AU - Katzenellenbogen, John A.
PY - 1997/6/23
Y1 - 1997/6/23
N2 - We describe the preparation of various 4-trifluoromethyl-substituted Δ3-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from α-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.
AB - We describe the preparation of various 4-trifluoromethyl-substituted Δ3-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from α-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.
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U2 - 10.1016/S0040-4039(97)00934-9
DO - 10.1016/S0040-4039(97)00934-9
M3 - Article
AN - SCOPUS:0030939349
SN - 0040-4039
VL - 38
SP - 4359
EP - 4362
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 25
ER -