New 4-spiroannulated tetrahydroisoquinolines by a one-pot sequential procedure. isolation and characterization of sigma-alkylpalladium heck intermediates |
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Authors: | Beccalli Egle M Broggini Gianluigi Martinelli Michela Masciocchi Norberto Sottocornola Silvia |
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Affiliation: | Istituto di Chimica Organica "A. Marchesini", Facoltà di Farmacia, Università di Milano, via Venezian 21, 20133 Milano, Italy. |
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Abstract: | A simple and efficient entry to new tetrahydroisoquinolines 4-spiroannulated to a five-membered heterocyclic ring has been achieved starting from secondary N-allylamines and involving sequential 2-iodobenzylation/intramolecular Heck reaction/1,3-dipolar cycloaddition. A variety of Heck cyclization conditions were surveyed. When using Pd(PPh(3))(4) as catalyst, stable sigma-alkylpalladium iodide complexes were isolated and characterizated. |
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