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Background

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Catalytic asymmetric cycloadditions of 1,3-dipoles to olefins have been utilized to prepare optically active five-membered heterocyclic ring systems that can contain up to four asymmetric centers, and therefore, are indispensable for the syntheses of biologically important heterocyclic compounds. During the last decade, highly enantioselective 1,3-dipolar cycloaddition reactions catalyzed by chiral Lewis acids have been developed for several 1,3-dipoles, such as nitrones, nitrile oxides, nitrile imines, diazoalkanes, and carbonyl ylides. We have developed the reactions catalyzed by 2,6-bis(oxazolinyl)pyridine (Pybox)-rare earth metal and binaphthyldiimine (BINIM)-Ni(II) complexes.

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