Abstract: The synthesis of various 5,5-disubstituted imidazolones and 5,5,2-trisubstituted imidazolones has been achieved. Two different methodologies have been developed by taking advantage of the rich reactivity of the isocyanide group. The reaction of α,α-disubstituted isocyanoacetate, primary amines in the presence of a catalytic amount of AgNO₃ afforded 5,5-disubstituted imidazolones in good to excellent yields. On the other hand, a bimetallic Cu^I/Pd^II catalyzed reaction of α,α-disubstituted isocyanoacetate, primary amines and aryl halide afforded 5,5,2-trisubstituted imidazolone in moderated to good yield. Finally, total synthesis of Rutacarpine and (±) Evodiamine featuring this methodology have been accomplished.

[1] Clemenceau, A.; Wang, Q.; Zhu, J. manuscript in preparation.