A Mild and Efficient Method for the One-Pot Monocarboxymethylation of Primary Amines
Timothy J. K. Gibbs, Michael Boomhoff, Nicholas C. O. Tomkinson*
*School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, UK, Email: tomkinsonnccardiff.ac.uk
T. J. K. Gibbs, M. Boomhoff, N. C. O. Tomkinson, Synlett, 2007, 1573-1575.
DOI: 10.1055/s-2007-982531
Abstract
A mild and efficient monocarboxymethylation of a broad range of primary amines takes place under aqueous conditions at room temperature. Treatment of primary amines with two equivalents of glyoxylic acid leads to N-formyl glycine derivatives. Subsequent hydrolysis of the crude reaction solution gives monocarboxymethylated products in very good yield.
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proposed mechanism
Key Words
metal-free synthesis, amino acids, glycine derivatives
ID: J60-Y2007-2040