{"id":291,"date":"2023-08-25T14:15:55","date_gmt":"2023-08-25T18:15:55","guid":{"rendered":"https:\/\/blog.richmond.edu\/downey\/?p=291"},"modified":"2023-08-25T14:15:55","modified_gmt":"2023-08-25T18:15:55","slug":"new-propargyl-amide-synthesis-published","status":"publish","type":"post","link":"https:\/\/blog.richmond.edu\/downey\/2023\/08\/25\/new-propargyl-amide-synthesis-published\/","title":{"rendered":"New Propargyl Amide Synthesis Published!"},"content":{"rendered":"<p>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 &#8217;23, Alex Helbling &#8217;23, and Remi Graff &#8217;26 for the mountain of successful research they put into <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403923004288?dgcid=author\">One-pot silyl imidate formation-N-alkylation reactions of amides with propargyl propionates<\/a>, 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&#8217;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&#8217;s impressive academic-year work ethic.<\/p>\n<p>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.<\/p>\n<p>The pdf of this paper is not the most aesthetically pleasing I&#8217;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.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>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 &#8217;23, Alex Helbling &#8217;23, and Remi Graff &#8217;26 for the mountain of successful research<\/p>\n","protected":false},"author":2955,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-291","post","type-post","status-publish","format-standard","hentry","category-uncategorized"],"jetpack_featured_media_url":"","_links":{"self":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts\/291","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/users\/2955"}],"replies":[{"embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/comments?post=291"}],"version-history":[{"count":1,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts\/291\/revisions"}],"predecessor-version":[{"id":292,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/posts\/291\/revisions\/292"}],"wp:attachment":[{"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/media?parent=291"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/categories?post=291"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/blog.richmond.edu\/downey\/wp-json\/wp\/v2\/tags?post=291"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}