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.
Gold(I) and Gold(III) catalyzed cycloaddition/cyclization reactions of vinylindoles with allenes / E. Rossi, G. Abbiati, M. Dell'Acqua, V. Pirovano - In: Congresso delle sezioni Toscana-Umbria-Marche-Abruzzo della società chimica italiana[s.l] : Società Chimica Italiana, 2016 Sep 25. - ISBN 9788886208789. - pp. 46-46 (( Intervento presentato al 35. convegno TUMA tenutosi a Giulianova nel 2016.
Gold(I) and Gold(III) catalyzed cycloaddition/cyclization reactions of vinylindoles with allenes
E. Rossi;G. Abbiati;M. Dell'Acqua;V. Pirovano
2016
Abstract
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.File | Dimensione | Formato | |
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