Stereocontrol in cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4-benzoylamino-5-phenylpyrazolidin-3-on-1-azomethine imines

Cycloadditions of (1Z,4R*,5R*)-4-benzoylamino-5-phenylpyrazolidin-3-on-1-azomethine imines to olefinic dipolarophiles were studied. Stereochemistry of cycloadditions to azomethine imines was found to be controlled by stereodirecting phenyl group at position 3, as well as by the ortho-substituents at the aromatic ring at position 1′. The structures of dipoles and products were confirmed by NMR and X-ray diffraction.