A Straightforward Entry to -Trifluoromethylated Allenamides and Their Synthetic Applications

作者：Guissart Celine; Dolbois Aymeric; Tresse Cedric; Saint Auret Sarah; Evano Gwilherm; Blanchard Nicolas

来源：Synlett, 2016, 27(18): 2575-2580.

DOI：10.1055/s-0035-1562518

• allenamides
• trifluoromethyl
• copper-mediated reaction
• isomerization
• radical reaction
• gold(I) catalysis

gamma-Trifluoromethylated allenamides were obtained in good to excellent yields through a base-induced isomerization from the corresponding protected trifluoromethylated propargylic amines. This 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 and a range of protecting groups on the nitrogen atom. The reactivity of the -trifluoromethylated allenamides was explored and they were found to be excellent substrates for radical- and gold(I)-catalyzed cyclizations yielding fluoro-alkylated nitrogen heterocycles.

• 出版日期2016-11