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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