Abstract
In this work, the reactivity of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one toward
primary aliphatic amines was studied. The reaction was found to be extremely selective
to synthesize a series of 1-alkyl-4-(aminoalkyl)-2-(trifluoromethyl)-1H-pyrroles (13 examples, up to 90% yield) and a series of highly functionalized β-enaminones
(6 examples, up to 78% yield), with only the amount of amine and the reaction conditions
needing to be controlled. The structure of the products was unambiguously determined
by single crystal X-ray diffraction and 2D NMR experiments.
Key words
pyrroles - trifluoromethyl group - enaminones - heterocycles - Michael addition
