The reaction of 1,3-dipolar cycloaddition of conjugated aryl(hetaryl) methylideneacetones, which containing various peripheral substituents, with azomethine ylides was carried out. It was established that the interaction is not chemoselective and proceeds with the participation of two non-equivalent reaction centers of dipolarophile with high diastereoselectivity. The products of cycloaddition were a mixture of structural isomers endo-cycloaddition. Monoenone transform to spyropyrrolidines with high endo-stereoselectivity.