三氟甲磺酸三甲基硅酯，Trimethylsilyl trifluoromethanesulfonate [TMSOTf, TMS]；99%

Trimethylsilyl trifluoromethanesulfonate has been used in combination with boron trifluoride etherate for the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers with organolithium reagents in the presence of a chiral ligand.
It can be used:

• As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.
• To activate benzyl and allyl ethers for the alkylation of sulfides.
• To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.
• To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.
• As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.

It may also be used to catalyze:

• Acylation of alcohols with acid anhydrides.
• Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.
• Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.