Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines

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Title: Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines
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: Organocatalysts | Enantioselective | Michael addition | α,α-disubstituted aldehydes | Maleimides
Knowledge Area: Química Orgánica
Issue Date: 15-Aug-2014
Publisher: Elsevier
Citation: Tetrahedron: Asymmetry. 2014, 25(15): 1091-1094. doi:10.1016/j.tetasy.2014.06.014
Abstract: Enantiomerically pure mono-N-Boc-protected trans-cyclohexa-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. Using a single enantiomer of the organocatalyst, both enantiomeric forms of the resulting Michael adducts bearing a new quaternary stereocenter are obtained in high yields, by only changing the reaction solvent from chloroform (up to 86% ee) to aqueous DMF (up to 84% ee).
Sponsor: We thank the financial support from the Spanish Ministerio de Economía y Competitividad (Project CTQ2011-24151), FEDER, the COST Action CM0905 ‘Organocatalysis’, and the University of Alicante.
URI: http://hdl.handle.net/10045/46332
ISSN: 0957-4166 (Print) | 1362-511X (Online)
DOI: 10.1016/j.tetasy.2014.06.014
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2014 Elsevier Ltd.
Peer Review: si
Publisher version: http://dx.doi.org/10.1016/j.tetasy.2014.06.014
Appears in Collections:INV - CESO - Artículos de Revistas

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