Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids

The one-pot reaction of natural amino acids (glycine, β-alanine, γ-aminobutyric and ɛ-aminocapronic acids, d,l-valine, d,l-leucine, anthranilic acid) with bielectrophilic acylacetylenes proceeds chemo-, regio- and stereospecifically in the presence of NaOH (45–50 °C, 4 h, EtOH–H2O) to give (after treatment of the reaction mixture with aqueous HCl) Z-isomers of N-acylvinyl derivatives of amino acids in 87–94% yield.