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Issue 6, 2013
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Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations

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Abstract

Carbon dioxide can be used as a temporary protecting group for amines. A carbamic acid is formed reversibly when CO2 is bubbled through a solution of a sufficiently basic primary amine at room temperature and atmospheric pressure. This reaction is employed for the protection of the amine functionality in several reactions at room temperature where inter- or intramolecular selectivity is desired. The concept is demonstrated for the selective Michael additions to methyl acrylate of a normally less reactive sulfonamide in the presence of a strong amine nucleophile, or of a cyclic secondary amine in the presence of an aliphatic primary amine, or of a β-ketoester in the presence of amines. The selective acylation of an alcohol in the presence of an amine can be achieved under a CO2 atmosphere as well.

Graphical abstract: Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations

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Publication details

The article was received on 25 Mar 2013, accepted on 11 Apr 2013 and first published on 11 Apr 2013


Article type: Paper
DOI: 10.1039/C3GC40568K
Citation: Green Chem., 2013,15, 1550-1557
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    Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations

    A. Peeters, R. Ameloot and D. E. De Vos, Green Chem., 2013, 15, 1550
    DOI: 10.1039/C3GC40568K

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