NIS-mediated ring-closure/opening cascade reactions of allylamides: an expedient route to oxazolines

An unprecedented NIS-mediated ring-closure/opening cascade reaction of allylamides is developed. The substrates with various functionalities were well tolerated and the scope can be extended to allylic carboxylates. Notably, the resulting iodinated chain products are versatile building blocks for the synthesis of oxazolines and epoxides. Furthermore, propargylamides can also undergo this reaction smoothly, providing the corresponding diiodoketones in good yields. The protocol offers a value route to explore new reaction patterns of other functionalized alkenes or alkynes.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide