N-trialkylsilyl bistrifluoromethanesulfonimides (R3SiNTf2) are powerful catalysts for the highly efficient alpha-amido alkylation reactions of silicon-based nucleophiles.

[reaction: see text] In situ formed N-trialkylsilyl bistrifluoromethanesulfonimides (R3SiNTf2) species have been shown to efficiently catalyze the nucleophilic substitution reactions of chiral 5-oxypyrrolidin-2-ones by silicon-based nucleophiles. The reaction rates were significantly accelerated in comparison to the cases where the usual triflate catalysts are used. Adducts were obtained in high yields and usual stereoselectivities within short reaction times, and the process was compatible with a semipreparative scale.