Good news from here at the University of Richmond. The excellent work of Grace Ann Robertson ’21, Matt Santa ’17, Kari Flicker ’18, and William Stith ’18 has produced a fine manuscript in Tetrahedron Letters! Matt and Will began this project one summer a few years ago, Kari carried it on, and Grace Ann finished it off in the summer of 2019. I even contributed a little bit myself while Grace Ann was out of the country.
We’ve developed a useful way of converting acetonitrile, when used in solvent quantities, into a mildly nucleophilic silyl ketene imine in the presence of TMSOTf and an amine base. When either an acetal or a nitrone is present, a TMSOTf-promoted Mukaiyama-like reaction takes place to yield beta-methoxynitriles or beta-aminonitriles, depending on the electrophile. The project grew out of some long-ago work with other nitriles by Carly Mueller ’14, Alice Lee ’16, and Jack Goodin ’18. Those were the days!