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.

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