Strong Lewis acid catalyst and highly reactive silylating agent with a much greater selectivity for C-silylation than chlorotrimethylsilane.1 It is used to cleave t-butyl esters directly to trimethylsilyl esters,2 promote chemoselective reactions of acyclic acetals in the presence of cyclic acetals,3 promote cycloaddition of nitrones with silyl enol ethers,4 catalyze the conversion of aldehydes to homoallyl ethers in an Ionic Liquid 5 and assist facile deprotection of N,O-Acetonides.6 Employed in the synthesis of enaminones as an Activator,7 one-pot synthesis of α-aminonitriles and their fluorinated analogues,8 and synthesis of N-vinyl derivatives of nucleobases as a Lewis acid catalyst.9
1. J. Prakt. Chem. 1999, 341, 410.
2. Org. Lett. 2002, 4, 1947.
3. J. Chem. Soc., Perkin Trans. 1, 1994, 2357.
4. J. Chem. Soc., Perkin Trans. 1, 1993, 3157.
5. Synthesis, 2005, 2661.
6. J. Org. Chem. 2007, 73, 752.
7. Synth. Commun. 1997, 27, 4275.
8. Synlett 2007, 2395.
9. Synthesis 2002, 0172.