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Closed Access item N-Arylmethyl-7-azabicyclo[2.2.1]heptane derivatives: synthesis and reaction mechanisms

Authors:Gómez, Elena
Marco-Contelles, José L.
Soriano, Elena
Jimeno, M. Luisa
Keywords:Bromination, Epibatidine analogues, Heterocyclization, N-(Arylmethyl)cyclohex-3-enamines, N-Arylmethyl-7-azabicyclo[2.2.1]heptanes, Reaction mechanisms
Issue Date:2009
Publisher:Elsevier
Citation:Tetrahedron 65 (45) : 9224-9232 (2009)
Abstract: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.
Publisher version (URL):http://dx.doi.org/10.1016/j.tet.2009.09.013
URI:http://hdl.handle.net/10261/34285
E-ISSNmetadata.dc.identifier.doi = DOI:00404020
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