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(PPh3)4 as catalyst, stable σ-alkylpalladium iodide complexes were isolated and characterizated.
New 4-spiroannulated tetrahydroisoquinolines by a one-pot sequential procedure : isolation and characterization of sigma-alkylpalladium Heck intermediates / E. Beccalli, G. Broggini, M. Martinelli, N. Masciocchi, S. Sottocornola. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 8:20(2006), pp. 4521-4524.
New 4-spiroannulated tetrahydroisoquinolines by a one-pot sequential procedure : isolation and characterization of sigma-alkylpalladium Heck intermediates
E. BeccalliPrimo
;M. Martinelli;
2006
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(PPh3)4 as catalyst, stable σ-alkylpalladium iodide complexes were isolated and characterizated.
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