An efficient and chemoselective Brønsted acidic ionic liquid-catalyzed N-Boc protection of amines

The first report of a Brønsted acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [(HMIm)BF 4], catalyzed efficient and chemoselective N-Boc protection of various amines using (Boc) 2O is presented. Optically pure amino alcohols and amino acid esters were converted efficiently to their corre...

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Bibliographic Details
Published in:Tetrahedron letters 2008-04, Vol.49 (16), p.2527-2532
Main Authors: Sunitha, Sadula, Kanjilal, Sanjit, Reddy, P. Srinivasa, Prasad, Rachapudi B.N.
Format: Article
Language:English
Subjects:
Amines
Brønsted acidic ionic liquid
Chiral amino acid esters
Chiral aminols
Di- tert-butyl pyrocarbonate
N-Boc protection
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Summary:The first report of a Brønsted acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [(HMIm)BF 4], catalyzed efficient and chemoselective N-Boc protection of various amines using (Boc) 2O is presented. Optically pure amino alcohols and amino acid esters were converted efficiently to their corresponding optically pure N-Boc derivatives. The reported method is mild, solvent-free and has the advantages of both homogeneous and heterogeneous catalysis with high product yields, selectivity and ease of product separation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.02.126