Ionic amino acids: Application as organocatalysts in the aza-Michael reaction

The ethyl methyl imidazolium salts of amino acids, [emim][AA], have been used as catalysts in the aza-Michael reaction. Furthermore, when chiral amino acids were used, a stereoselective reaction was achieved. The mechanism of the transformation was verified by the detection of a key intermediate by electrospray ionization mass spectroscopy (ESI-MS).

Graphical abstractThe ethyl methyl imidazolium salts of amino acids, [emim][AA], was used as catalysts in the aza-Michael reaction. When chiral amino acids were used, a stereoselective reaction was achieved.Figure optionsDownload full-size imageDownload high-quality image (75 K)Download as PowerPoint slideHighlights► [emim][AA] worked as a catalyst in aza-Michael reactions. ► The chiral ionic amino acid could promote the asymmetric reaction. ► Reaction mechanism was investigated using ESI-MS.