Trimethylsilyl trifluoromethanesulfonate
Trimethylsilyl trifluoromethanesulfonate is a trifluoromethanesulfonate derivate with a trimethylsilyl R-group. It has similar reactivity to trimethylsilyl chloride, and is also used often in organic synthesis.Examples of use
A common application is the conversion of ketones and aldehydes to silyl enol ethers.
The stereoselective synthesis of seven benzylated proanthocyanidin trimers -epicatechin--epicatechin trimer, catechin--catechin--catechin trimer, epicatechin--epicatechin--catechin trimer and epicatechin--catechin- can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. Deprotection of -catechin and -epicatechin trimers derivatives gives four natural procyanidin trimers in good yields.
It has been used in Takahashi Taxol total synthesis or for chemical glycosylation reactions.Related reagents
Trimethylsilyl trifluoromethanesulfonate is a source of trimethylsilyl cation. Other more potent sources silylium cations are known.
