Powerful silylating agent and Lewis acid; compare tert-Butyl-dimethyl-chlorosilane. Silylation of hindered alcohols can be effected with TBDMS-OTf and 2,6-lutidine, where other reagents are unsuccessful: Tetrahedron Lett., 22, 3455 (1981). Has been used in a sequence for the conversion of N-Boc to N-Cbz: Tetrahedron Lett., 26, 5543 (1985). Treatment of ɑ?-unsaturated esters containing a suitably-placed ketone function with the reagent and triethylamine results in tandem intramolecular Michael-aldol reactions to give cyclobutanone derivatives: J. Am. Chem. Soc., 115, 8107 (1993). For general reactions of trialkylsilyl perfluoroalkanesulfonates, see Trimethyl-silyl- trifluoromethanesulfonate; reviews: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).
