Bifunctional primary amine 2-aminobenzimidazole organocatalyst anchored to trans-cyclohexane-1,2-diamine in enantioselective conjugate additions of aldehydes
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Title: | Bifunctional primary amine 2-aminobenzimidazole organocatalyst anchored to trans-cyclohexane-1,2-diamine in enantioselective conjugate additions of aldehydes |
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Authors: | Fernandes, Talita de A. | Vizcaíno-Milla, Pascuala | Ravasco, João M.J.M. | Ortega-Martínez, Aitor | Sansano, Jose M. | Nájera, Carmen | Costa, Paulo R.R. | Fiser, Béla | Gómez Bengoa, Enrique |
Research Group/s: | Síntesis Asimétrica (SINTAS) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica |
Keywords: | Bifunctional | Enantioselective | Aldehydes |
Knowledge Area: | Química Orgánica |
Issue Date: | 15-Feb-2016 |
Publisher: | Elsevier |
Citation: | Tetrahedron: Asymmetry. 2016, 27(2-3): 118-122. doi:10.1016/j.tetasy.2015.12.004 |
Abstract: | Bifunctional chiral primary amine 8 containing an (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-benzimidazole unit is used as a general organocatalyst for the Michael addition of α,α-branched aldehydes to nitroalkenes and maleimides. The reactions take place, with 20 mol % of catalyst in dichloromethane at rt for nitroalkenes and with 15 mol % catalyst loading in toluene at 10 °C for maleimides, in good yields and enantioselectivities. DFT calculations demonstrate the bifunctional character of this organocatalyst activating the aldehyde by enamine formation and the Michael acceptor by double hydrogen bonding. |
Sponsor: | The Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), the Basque Government (GV Grant IT-291-07), the FP7 Marie Curie Actions of the European Commission via the ITN ECHONET network (MCITN-2012-316379) and the Universities of Alicante and Basque Country are gratefully acknowledged for financial support. We also thank for technical and human support provided by IZO-SGI SGIker of UPV-EHU and European funding (ERDF and ESF). Financial support from Brazilian agencies CAPES-DGU (Project 200/09), CNPq, FAPERJ and UFRJ are also acknowledged. A. O. M. thanks MINECO for a FPI fellowship (BES-2014-069695). |
URI: | http://hdl.handle.net/10045/52712 |
ISSN: | 0957-4166 (Print) | 1362-511X (Online) |
DOI: | 10.1016/j.tetasy.2015.12.004 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2015 Elsevier Ltd. |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1016/j.tetasy.2015.12.004 |
Appears in Collections: | INV - SINTAS - Artículos de Revistas |
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2016_Fernandes_etal_TetAsy_final.pdf | Versión final (acceso restringido) | 981,23 kB | Adobe PDF | Open Request a copy |
2016_Fernandes_etal_TetAsy_rev.pdf | Versión revisada (acceso abierto) | 1,37 MB | Adobe PDF | Open Preview |
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