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Título : N-Arylmethyl-7-azabicyclo[2.2.1]heptane derivatives: synthesis and reaction mechanisms
Autor : Gómez, Elena, Marco-Contelles, José L., Soriano, Elena, Jimeno, M. Luisa
Palabras clave : Bromination
Epibatidine analogues
Reaction mechanisms
Fecha de publicación : 2009
Editor: Elsevier
Resumen: N-Arylmethyl-7-azabicyclo[2.2.1]heptane (I) derivatives have been synthesized by deprotection of N-protected, N-(arylmethyl)cyclohex-3-enamines, bromination of the resulting secondary cyclohex-3-enamines, followed by base-promoted cyclization (route a), or by bromination of N-protected, N-(arylmethyl)cyclohex-3-enamines followed by deprotection and base-mediated cyclization (route b). In these protocols we have observed that the bromination of the key intermediates (12, 13, and 19) is stereoselective leading to major trans-3-cis-4-dibromides (14, 17, and 20), whose mild base-mediated heterocyclization (on compound 14), or the two-step acid hydrolysis plus base-promoted cyclization (on compounds 17 and 20), gave products 6 and 7 in good yield. A mechanistic investigation using DFT has been carried out to explain the results observed in this work. © 2009 Elsevier Ltd. All rights reserved.
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DOI: 10.1016/j.tet.2009.09.013
Citación : Tetrahedron 65 (45) : 9224-9232 (2009)
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