A Straightforward Entry to gamma-Trifluoromethylated Allenamides and their Synthetic Applications

gamma-Trifluoromethylated allenamides were obtained in good to excellent yields through a base-induced isomerization from the corresponding protected trifluoromethylated propargylic amines. The method, which simply required the treatment of the starting propargylic amines with sodium hydroxide in THF, was found to be fairly general and tolerates various alkyl and aryl substituents on the nitrogen atom and a range of protecting groups. The reactivity of the gamma-trifluoromethylated allenamides was explored and they were found to be excellent substrates for radical- and gold(I)-catalysed cyclizations yielding to fluoroalkylated nitrogen heterocycles.
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