Palladium-Catalyzed Ring Opening of Aminocyclopropyl Ugi Adducts

Abstract

The ring opening of aminocyclopropanes triggered by activation with an intramolecular arylpalladium(II) iodide complex is an interesting strategy for the synthesis of nitrogen heterocycles and a valuable Ugi postcondensation-type transformation. Six- and seven-membered-ring cyclic enamines may be obtained.

Key words

aminocyclopropanes - ring opening - palladium - Ugi - Ugi-Smiles

References and Notes

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10

The regioselectivity observed with aryl-substituted amino-cyclopropanes may be explained by a productive interaction of the aryl-Pd(II)I intermediate through the less hindered approach of the cyclopropyl ring. Further insights into the potential electronic effects of the aryl moiety should be addressed by comparison with alkyl-substituted cyclo-propanes.