6π/10π-Electrocyclization of ketene-iminium salts for the synthesis of substituted naphthylamines

E Villedieu-Percheron, S Catak, D Zurwerra…

Index: Villedieu-Percheron, Emmanuelle; Catak, Saron; Zurwerra, Didier; Staiger, Roman; Lachia, Mathilde; De Mesmaeker, Alain Tetrahedron Letters, 2014 , vol. 55, # 15 p. 2446 - 2449

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Citation Number: 4

Abstract

Abstract An intramolecular 6π/10π-electrocyclization from ketene-iminium salts was developed for the preparation of naphthylamines. Various substituents on the nitrogen, on the aromatic ring, and on the olefin were studied. Tricyclic skeletons were obtained in few steps and good overall yields. The electrocyclization of ketene-iminium salts has been computationally explored by means of DFT calculations and their activation barriers were ...

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