Enantioselective Michael addition of isobutyraldehyde to nitroalkenes organocatalyzed by chiral primary amine-guanidines
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http://hdl.handle.net/10045/37268
Title: | Enantioselective Michael addition of isobutyraldehyde to nitroalkenes organocatalyzed by chiral primary amine-guanidines |
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Authors: | Ávila Freire, Ángel | Chinchilla, Rafael | Fiser, Béla | Gómez Bengoa, Enrique | Nájera, Carmen |
Research Group/s: | Síntesis Asimétrica (SINTAS) | Catálisis Estereoselectiva en Síntesis Orgánica (CESO) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Enantioselective Michael addition | Isobutyraldehyde | Nitroalkenes | Organocatalyzed | Chiral primary amine-guanidines |
Knowledge Area: | Química Orgánica |
Issue Date: | 15-Mar-2014 |
Publisher: | Elsevier |
Citation: | Tetrahedron: Asymmetry. 2014, 25(5): 462-467. doi:10.1016/j.tetasy.2014.02.006 |
Abstract: | Primary amine-guanidines derived from trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of isobutyraldehyde to arylated and heteroarylated nitroalkenes. The reaction was performed in the presence of imidazole as the additive in aqueous DMF as the solvent at 0 °C. The corresponding Michael adducts bearing a new stereocenter were obtained in high yields and with enantioselectivities of up to 80%. Theoretical calculations are used to justify the observed sense of the stereoinduction. |
Sponsor: | Spanish Ministerio de Economía y Competitividad (projects CTQ2010-20387, CTQ2010-21263-C02 and Consolider Ingenio 2010, CSD2007-00006), FEDER, the COST Action CM0905 ‘Organocatalysis’, the Generalitat Valenciana (Prometeo/2009/039), 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 the Basque Country. |
URI: | http://hdl.handle.net/10045/37268 |
ISSN: | 0957-4166 (Print) | 1362-511X (Online) |
DOI: | 10.1016/j.tetasy.2014.02.006 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1016/j.tetasy.2014.02.006 |
Appears in Collections: | INV - SINTAS - Artículos de Revistas INV - CESO - Artículos de Revistas |
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2014_Avila_etal_Tetrahedron-Asymmetry_final.pdf | Versión final (acceso restringido) | 764,71 kB | Adobe PDF | Open Request a copy |
2014_Avila_etal_Tetrahedron-Asymmetry.pdf | Versión revisada (acceso abierto) | 363,77 kB | Adobe PDF | Open Preview |
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