Palladium-catalyzed allylation of trifluoromethylated ketene aminoacetals

•Trifluoromethylated ketene aminoacetals were prepared.•Pd-catalyzed allylation was carried out.•Asymmetric reaction was researched.•Quaternary carbon centers were built.

A new development in the palladium-catalyzed allylation reaction of trifluoromethylated ketene aminoacetals was reported. These nucleophilic reagents were prepared by adding aminoalcohols to methyl 3,3,3-trifluoro-2-trifluoromethylpropanoate. The asymmetric version of the allylation reaction was investigated using chiral oxazolidine-based starting materials or chiral palladium catalysts. Asymmetric allylic alkylation was carried out with up to 74% ee using a chiral catalyst. However, no improvement was observed using double stereodifferentiation. These results provided a novel access for trifluoromethylated all-carbon quaternary carbon centers.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide