Chemistry - A European Journal p. 17578 - 17582 (2015)
Update date:2022-08-11
Topics:
Romanini, Simone
Galletti, Emilio
Caruana, Lorenzo
Mazzanti, Andrea
Himo, Fahmi
Santoro, Stefano
Fochi, Mariafrancesca
Bernardi, Luca
A domino Friedel-Crafts/nitro-Michael reaction between 4-substituted indoles and nitroethene is presented. The reaction is catalyzed by BINOL-derived phosphoric acid catalysts, and delivers the corresponding 3,4-ring-fused indoles with very good results in terms of yields and diastereo- and enantioselectivities. The tricyclic benzo[cd]indole products bear a nitro group at the right position to serve as precursors of ergot alkaloids, as demonstrated by the formal synthesis of 6,7-secoagroclavine from one of the adducts. DFT calculations suggest that the outcome of the reaction stems from the preferential evolution of a key nitronic acid intermediate through a nucleophilic addition pathway, rather than to the expected "quenching" through protonation.
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