Palladium-Catalyzed Allylation of Isocyanoacetates with Vinyl-Aziridines

The first palladium-catalyzed allylation of isocyanoacetates with vinyl aziridines has been developed. The reaction conditions were suitable for a variety of alpha-aryl isocyanoacetates as well as N-substituted vinyl aziridines, affording the corresponding allylation products in moderate to high yields (up to 98 %) along with excellent stereoselectivity and regioselectivity. Transformations of the allylation products into trans-4,5-dehydrolysine analogues and a highly functionalized proline ester derivative were further demonstrated, and a preliminary asymmetric version of the reaction has also been evaluated. A practical and efficient protocol has been developed for the direct synthesis of alpha-allylated isocyanoacetates through palladium-catalyzed highly regio- and stereoselective allylation of alpha-isocyanoacetates with vinyl aziridines under mild conditions. image