Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds
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Title: | Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds |
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Authors: | Benavent, Llorenç | Puccetti, Francesco | Baeza, Alejandro | Gómez-Martínez, Melania |
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: | Organocatalysis | Electrophilic amination | Guanidines | Asymmetric catalysis | Dicarbonyl compounds |
Knowledge Area: | Química Orgánica |
Issue Date: | 11-Aug-2017 |
Publisher: | MDPI |
Citation: | Benavent L, Puccetti F, Baeza A, Gómez-Martínez M. Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds. Molecules. 2017; 22(8):1333. doi:10.3390/molecules22081333 |
Abstract: | The synthesis and the evaluation as organocatalysts of new chiral guanidines derived from benzimidazoles in the enantioselective α-amination of 1,3-dicarbonyl compounds using di-t-butylazodicarboxylate as aminating agent is herein disclosed. The catalysts are readily synthesized through the reaction of 2-chlorobezimidazole and a chiral amine in moderate-to-good yields. Among all of them, those derived from (R)-1-phenylethan-1-amine (1) and (S)-1-(2-naphthyl)ethan-1-amine (3) turned out to be the most efficient for such asymmetric transformation, rendering good-to-high yields and moderate-to-good enantioselectivities for the amination products. |
Sponsor: | Financial support from the University of Alicante (VIGROB-173, VIGROB-285, GRE12-03, UAUSTI13-01, UAUSTI13-02), and Spanish Ministerio de Economía y Competitividad (CTQ2011-24151) is acknowledged. |
URI: | http://hdl.handle.net/10045/68751 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules22081333 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.3390/molecules22081333 |
Appears in Collections: | INV - MATCAT - Artículos de Revistas INV - AMIC - Artículos de Revistas |
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2017_Benavent_etal_Molecules.pdf | 1,15 MB | Adobe PDF | Open Preview | |
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