Intramolecular Bromoamination of Conjugated N-Tosylaminodienes Using N-Bromosuccinimide. Synthesis of Bromoallyl-Substituted N-Heterocycles and Their Applications as Building Blocks

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Title: Intramolecular Bromoamination of Conjugated N-Tosylaminodienes Using N-Bromosuccinimide. Synthesis of Bromoallyl-Substituted N-Heterocycles and Their Applications as Building Blocks
Authors: Márquez Segovia, Isabel | Baeza, Alejandro | Otero, Antonio | Nájera, Carmen
Research Group/s: Síntesis Asimétrica (SINTAS) | Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Nitrogen heterocycles | Halo­amination | Halogens | Electrophilic addition | Cyclization
Knowledge Area: Química Orgánica
Issue Date: Aug-2013
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2013, 2013(22): 4962-4970. doi:10.1002/ejoc.201300444
Abstract: The bromonium-promoted cyclization of conjugated aminodienes is described. The reaction proceeds smoothly in the presence of N-bromosuccinimide as halonium promoter, and using N-tosyl-protected aminodienes as substrates, to give the corresponding halocyclization products in high yields and with high diastereoselectivities. It can be envisaged that the formation of these products is the result of an SN2′-type ring-opening of a terminal bromonium intermediate in a 5-exo-trig or 6-exo-trig cyclization mode. The presence of an allyl bromide moiety in the haloamination products makes these molecules highly attractive from a synthetic point of view, as it opens the way for further transformations. Thus, allylic substitution reactions with different nucleophiles (acetate, azide, cyanide, and malonate), palladium-catalysed Suzuki coupling, and silver-mediated bromine displacement reactions were carried out successfully.
Sponsor: The Spanish Ministerio de Ciencia e Innovación (MICINN) [projects CTQ2010-20387 and Consolider Ingenio 2010, CSD2007-00006 and Juan de la Cierva contract (to A. B.), JCI-2009-03710], Fondos Europeos para el Desarrollo Regional (FEDER), the Generalitat Valenciana (PROMETEO 2009/039), and the University of Alicante are gratefully acknowledged for financial support.
URI: http://hdl.handle.net/10045/40227
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201300444
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/ejoc.201300444
Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - SINTAS - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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