Ru(II)/Organo Relay Catalytic Three-Component Reaction of 3-Diazooxindoles, Amines, and Nitroalkene: Formal Synthesis of (-)-Psychotrimine.

A highly enantioselective carbenoid-associated N-H functionalization/Michael addition cascade reaction is developed by virtue of Ru(II)/chiral organo bifunctional catalyst relay catalysis. In this way, a variety of optically pure 3-amino-3-alkyloxindoles can be easily achieved. Moreover, on the basis of this metal/organo relay catalytic three-component protocol, a key intermediate for the formal synthesis of (-)-psychotrimine could be obtained in six steps with 25% overall yield.