Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes

Rösner C., Hennecke U.

Abstract

An efficient method for the halocyclization of cyclopropanes has been developed. The cyclopropanes undergo a 1,3-addition reaction to form homohalocyclization products compared to conventional alkene halocyclizations. The reaction can be induced by various electrophilic halogenating agents including 1,3-dibromo-5,5-dimethylhydantoin and N-iodosuccinimide. In cyclopropane derivatives with a preexisting stereocenter, excellent induced diastereoselectivities can be observed. (Chemical Equation Presented).