Per(poly) fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels-Alder reaction

Ahighly diastereoselective three-component inverse-electron-demand aza Diels-Alder reaction assisted by per(poly) fluoroalkanesulfinamides is presented, providing a broad spectrum of highly functionalized piperidine derivatives with excellent endo/exo and facial diastereoselectivities. The electron-withdrawing perfluoroalkyl groups are crucial for the success of this reaction under mild conditions and facilitate monitoring the process and stereoselectivities of the reaction. The synthetic potential of these cycloadducts is also highlighted.