Asymmetric organocatalytic synthesis of Bisindoles - Scope and Derivatizations

Starting from 3 vinylindoles and glyoxolate imines we created a library of diverse 4,6-bis(1H-indole-3-yl)piperidine 2 carboxylates using 10 mol% of a chiral phosphoric acid. Utilising electron withdrawing groups on the starting material during the reaction led to the formation of Povarov-type structures, which extended the previous library of molecules. Furthermore we could demonstrate that consecutive reactions like reductions, cross coupling reactions or click reactions on bisindoles are feasible.

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