An additive‐free three‐component reaction of allenamides with in situ generated trifluoromethylnitrones has been uncovered. The reaction afforded an interesting class of trifluoromethylated methyleneisoxazolidines under mild conditions. Additionally, a gram‐scale reaction and the reductive transformation of trifluoromethylated isoxazolidines to aminomethylated allyl alcohol illustrate the high synthetic utility of the present synthetic strategy.