Synthesis of Aminoindolizidines through the Chemoselective and Diastereoselective Catalytic Hydrogenation of Indolizines

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Title: Synthesis of Aminoindolizidines through the Chemoselective and Diastereoselective Catalytic Hydrogenation of Indolizines
Authors: Albaladejo Maricó, María José | González Soria, María José | Alonso, Francisco
Research Group/s: 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: Synthesis | Aminoindolizidines | Chemoselective | Diastereoselective | Catalytic hydrogenation | Indolizines
Knowledge Area: Química Orgánica
Issue Date: 29-Sep-2016
Publisher: American Chemical Society
Citation: The Journal of Organic Chemistry. 2016, 81(20): 9707-9717. doi:10.1021/acs.joc.6b01782
Abstract: Indolizidines are bioactive heterocyclic compounds of great potential normally prepared following multistep routes. However, to the best of our knowledge, the synthesis of 1-aminoindolizidines has never been reported. Herein, 1-(dialkylamino)-3-substituted indolizidines have been straightforwardly synthesized using an atom-economic protocol that involves a copper-catalyzed three-component synthesis of indolizines followed by heterogeneous catalytic hydrogenation. The latter was found to be chemoselective using platinum(IV) oxide as the catalyst at 3.7 atm, providing the aminoindolizidines in modest-to-high yields (35–95%) and high diastereoselectivity (92:8 to >99:1). It has been experimentally demonstrated that the hydrogenation occurs through the intermediate 5,6,7,8-tetrahydroindolizine, which contains a pyrrole moiety. Moreover, the diastereomerically pure 1-(dibenzylamino)-3-substituted indolizidines could be further transformed into the corresponding monobenzylated or fully debenzylated aminoindolizidines by selective hydrogenolysis catalyzed by Pt/C or Pd/C, respectively, under ambient conditions.
Sponsor: This work was generously supported by the Spanish Ministerio de Economía y Competitividad (MINECO, CTQ2011-24151). M.J.A. and M.J.G.-S. acknowledge the Instituto de Síntesis Orgánica (ISO) of the Universidad de Alicante for both grants.
ISSN: 0022-3263 (Print) | 1520-6904 (Online)
DOI: 10.1021/acs.joc.6b01782
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2016 American Chemical Society
Peer Review: si
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Appears in Collections:INV - MATCAT - Artículos de Revistas

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