Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents
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Title: | Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents |
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Authors: | Flores Ferrándiz, Jesús | Chinchilla, Rafael |
Research Group/s: | 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: | Organocatalytic | Enantioselective | Conjugate addition | Aldehydes | Maleimides | Deep eutectic solvents |
Knowledge Area: | Química Orgánica |
Issue Date: | 15-Feb-2017 |
Publisher: | Elsevier |
Citation: | Tetrahedron: Asymmetry. 2017, 28(2): 302-306. doi:10.1016/j.tetasy.2016.12.009 |
Abstract: | The conjugate enantioselective addition of aldehydes, mainly α,α-disubstituted, to maleimides leading to enantioenriched succinimides, has been achieved in recyclable deep eutectic solvents at room temperature. Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as organocatalysts, affording high yields and up to 94% ee of the final succinimides. The product can be extracted from the deep eutectic solvent, which retains the chiral organocatalyst, allowing both the solvent and catalyst to be reused. |
Sponsor: | We thank the financial support from the Spanish Ministerio de Economía y Competitividad (project CTQ2015-66624-P) and the University of Alicante (VIGROB-173 and UAUSTI14). J. F.-F. particularly acknowledges the Vicerrectorado de Investigación y Transferencia de Conocimiento of the University of Alicante for a fellowship. |
URI: | http://hdl.handle.net/10045/66496 |
ISSN: | 0957-4166 (Print) | 1362-511X (Online) |
DOI: | 10.1016/j.tetasy.2016.12.009 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2016 Elsevier Ltd. |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1016/j.tetasy.2016.12.009 |
Appears in Collections: | INV - CESO - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2017_Flores_Chinchilla_TetraAsym_final.pdf | Versión final (acceso restringido) | 497,66 kB | Adobe PDF | Open Request a copy |
2017_Flores_Chinchilla_TetraAsym_rev.pdf | Versión revisada (acceso abierto) | 1,21 MB | Adobe PDF | Open Preview |
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