Friends, I write to share with you the excellent news that the Downey group has authored another publication. Please offer your best congratulations to Tyler Chong ’23, Alex Helbling ’23, and Remi Graff ’26 for the mountain of successful research they put into One-pot silyl imidate formation-N-alkylation reactions of amides with propargyl propionates, newly published in Tetrahedron Letters. This was a project where everything seemed to go right almost from the start, thanks to the ground-breaking discoveries of Alex Helbling, the incredibly productivity and insight of Tyler Chong, and Remi Graff’s ability to finish off a couple of the most difficult lingering challenges of the project. While some projects stretch out over five or six years, this one was done in just in a couple of summers thanks to Tyler’s impressive academic-year work ethic.
In this publication we show that amides can be transformed, briefly, into silyl imidates under our reaction conditions to generate a nitrogen-based nucleophile analogous to an enol silane. The TMSOTf in the reaction conditions also serves to activate a propargyl carboxylate through ionization to make a carbocation, and that carbocation reacts with the silyl imidate to produce an N-propargylated amide. And you can tell that to all your friends.
The pdf of this paper is not the most aesthetically pleasing I’ve ever seen, but we are proud to have this chemistry published in such a respected journal and we look forward to seeing where this branch of chemistry takes us next.