Gold(I) and Gold(III) catalyzed cycloaddition/cyclization reactions of vinylindoles with allenes

In the last year we developed several strategies to access carbazole derivatives through [4+2] cycloaddition reactions of 2-vinylindoles with allenes under gold catalysis. Application of cationic gold(I) and gold(III) catalysts as -activators allowed for the chemo-, regio- and diastereoselective construction of complex and intriguing architectures. More recently we are focusing on the enantioselective version of these and related reactions. In particular, we are currently studying the enantioselective version of our cascade reaction between 2-vinylindoles and propargyl esters and between a new class of 2-vinylindoles bearing a methyl group at C-3 position with allenamides for the synthesis, respectively, of enantioenriched tetrahydrocarbazoles and dearomatized indole derivatives. A complete survey of catalyst/ligand screening as well as scope and proposed reaction mechanisms will be reported.