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Issue 6, 2014
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Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds

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Abstract

A highly stereoselective organocatalytic Michael addition of aldehydes to trans-β-nitrostyrenes using PEG as a recyclable solvent medium is presented. The scope of this organocatalytic system is demonstrated by the formation of several Michael adducts in good yields and stereoselectivities. Furthermore, applying this new protocol to acetaldehyde, we have disclosed an easy formal synthesis of (R)-pregabalin, (R)-phenibut and (R)-bacoflen with good yields and outstanding enantioselectivities.

Graphical abstract: Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds

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Publication details

The article was received on 20 Jan 2014, accepted on 25 Mar 2014 and first published on 27 Mar 2014


Article type: Paper
DOI: 10.1039/C4GC00098F
Author version available: Download Author version (PDF)
Citation: Green Chem., 2014,16, 3169-3174
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    Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds

    K. S. Feu, A. F. de la Torre, S. Silva, M. A. F. de Moraes Junior, A. G. Corrêa and M. W. Paixão, Green Chem., 2014, 16, 3169
    DOI: 10.1039/C4GC00098F

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