Probably the most work-intensive TMSOTf project we’ve ever completed has just been published in the Journal of Organic Chemistry. Major congratulations are in order for the three students who put together this very important study: Danielle Confair ’16, Yiqi Liu ’18, and Elizabeth Heafner ’19.
These students have used TMSOTf to activate an acetate or propionate group to generate a resonance-stabilized carbocation, and they form the enol silane nucleophile under those same reaction conditions. The products are beta-alkynyl ketones that can be easily cyclized to form trisubstituted furans. Danielle, Yiqi, and Elizabeth did very careful work over the course of three years to bring this project completion. You can find a full description now in the pages of The Journal of Organic Chemistry.
Just click here to access the paper on the JOC website.