Synthesis of Aminoindolizidines through the Chemoselective and Diastereoselective Catalytic Hydrogenation of Indolizines
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http://hdl.handle.net/10045/61968
Title: | Synthesis of Aminoindolizidines through the Chemoselective and Diastereoselective Catalytic Hydrogenation of Indolizines |
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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. |
URI: | http://hdl.handle.net/10045/61968 |
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 |
Publisher version: | http://dx.doi.org/10.1021/acs.joc.6b01782 |
Appears in Collections: | INV - MATCAT - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2016_Albaladejo_etal_JOC_final.pdf | Versión final (acceso restringido) | 1,61 MB | Adobe PDF | Open Request a copy |
2016_Albaladejo_etal_JOC_preprint.pdf | Preprint (acceso abierto) | 1,18 MB | Adobe PDF | Open Preview |
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