Trimethylsilyl trifluoromethanesulfonate synthesis, trifluoromethanesulfonic acid

Trimethylsilyl trifluoromethanesulfonate (trimethylsilyl triflate) is the most synthetically useful representative of the family of trialkylsilyl perfluoroalkane-sulfonates (for a review, see reference 101) This reagent is commercially available or can be prepared easily by the reaction of chlorotrimethylsilane and triflic acid [101] It has wide application in organic synthesis as an excellent silylating reagent... 

After the readily available Friedel-Crafts catalyst, tin(IV) chloride, had been established as a catalyst for nucleoside synthesis, several other new catalysts, such as trimethylsilyl triflate (trimethylsilyl trifluoromethanesulfonate TMSOTf), etc., which are less acidic as Lewis acids... 

In the presence of an amino acid-derived boronate (e.g. 2) or a diamine-tin(II), complex,as Lewis acids, optically active aldol products are obtained in good yields (eq 8). In the addition of KSAs to iminies, a diphosphonium ditriflate (eq 9) or an acidic montmorillonite clay has been claimed to give better results than the originally reported Lewis acids (titanium(IV) chloride and trimethylsilyl trifluoromethanesulfonate ). The products of this reaction are valuable intermediates for the synthesis of p-lactams. Two excellent reviews covering this area have recently appeared. ... 

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