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

Literature Information

Publication Date 2013-04-11
DOI 10.1039/C3GC40568K
Impact Factor 10.182
Authors

Annelies Peeters, Rob Ameloot, Dirk E. De Vos


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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.

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