Synthesis of Chiral Heterocyclic N-Haloamides and -imides and Their Applications as Halogenating Agents and Mechanistic Probes

N-Haloamides and -imides are standard halogenating agents and have been used in radical as well as electrophilic halogenation reactions. Despite their many applications, there are only few reports of chiral derivatives of the most common of these reagents such as N-halosuccinimides. Herein, we report the synthesis of new chiral N-halogenated amides and imide derivatives, which are easily accessible from inexpensive starting materials of the chiral pool. These new chiral halogenating agents were then applied as stoichiometric reagents in halo-etherification reactions and as mechanistic probes in organo-catalytic halocyclization reactions.