New highly electrophilic gem- and spiro-activated trichloromethylnitrocyclopropanes were obtained by the Michael-initiated ring closure (MIRC) reaction of 1-bromo-1-nitro-3,3,3-trichloropropene with linear and cyclic CH-acids catalyzed by bases. Conditions for obtaining the target cyclopropanes were optimized. The process is characterized by high diastereoselectivity and allows obtaining cyclopropanes with trans-configuration of -NO 2 and -CCl 3 groups. Monocyclic (based on malonic acid dinitrile, methyl cyanoacetate, ethyl cyanoacetate, benzoylacetonitrile), spirocarbo- (based on 1,3-indanedione) and spiroheterocyclic (based on Meldrum's acid, dimethylbarbituric acid, 3-methyl-1-phenyl-5-pyrazolone) cyclopropane structures were isolated and characterized.