The ability of TMSOTf to act as both a Lewis acid and a silylating agent makes it a powerful choice in new reaction development. Because it can play two or more roles in a reaction, it can be used to develop so-called “one-pot” reactions, where two or more reactions take place in a single reaction flask without the need for purification of any intermediate compounds. This process greatly increases the efficiency of a synthetic route by shortening the time required and reducing the waste that would be generated in purification processes. Furthermore, the reaction products are often isolated as protected O-silylated products, which are useful for further synthetic steps.
Our work is currently funded by generous contributions from the Camille & Henry Dreyfus Foundation, the American Chemical Society-Petroleum Research Fund, and the University of Richmond. Previous sources of funding include the National Science Foundation, Research Corporation, and the Thomas F. and Kate Miller Jeffress Trust.
“One-pot silyl ketene acetal-formation-Mukaiyama–Mannich additions to imines mediated by trimethylsilyl trifluoromethanesulfonate” C. Wade Downey, Jared A. Ingersoll,* Hadleigh M. Glist,* Carolyn M. Dombrowski,* Adam T. Barnett* European Journal of Organic Chemistry 2015, 7287-7291.
* denotes undergraduate coauthor