The site-selective and regioselective allylation of 2-substituted indoles was performed by using a ruthenium(IV) precatalyst containing a phosphine-sulfonate chelate. Mono-, di-, and triallylated indoles were selectively obtained depending on the reaction conditions with the formation of water as the only byproduct. The preparation of 3-oxindole derivatives was then successfully performed owing to air oxidation of the corresponding allylated indoles. Diallylated pseudoindoxyls were proven to be good synthons to perform cyclization through a ring-closing metathesis reaction to afford the corresponding tricyclic adducts. The photophysical properties of the 3-oxindoles were measured, and some of the compounds showed strong fluorescence in water.

This manuscript reports on a suitable method for the synthesis of paracyclophane type, ferrocene-bridged chiral phosphoric acids, which bear silyl-substituents on their paracyclophane frameworks. These acids have been obtained easily in enantiomerically pure form, by taking advantage of (S)-(1-phenyl-2-cyanoethyl)phosphorodiamidite as a phosphorylating agent. They have been used then as catalysts for aza-Friedel-Crafts reactions between indoles and imines, giving high catalytic activity and up to 98% enantiomeric excess.