t-Butyl α-Lithiobis(trimethylsilyl)acetate

Uses

T-Butyl a-Lithiobis(trimethylsilyl)acetate reacts with aldehydes to form α-silylated vinyl esters.

Synthesis

Synthesis method of t-Butyl α-Lithiobis(trimethylsilyl)acetate: An approximately 1 M solution in THF is prepared by addition of t-butyl bis(trimethylsilyl)acetate to a 1.0 M solution of Lithium Diisopropylamide maintained at -78 °C. The solution is stirred for 1 h at -78 °C following complete addition.¹ A simplified procedure utilizes n-Butyllithium in place of LDA and produces the amine-free reagent in THF/hexane.²

Synthesis Reference(s)

1. Hartzell, S. L.; Rathke, M. W. TL 1976, 2737.
2. Sato, Y.; Takeuchi, S. S 1983, 734.