Chemo-, regio- and stereospecific addition of amino acids to acylacetylenes: a facile synthesis of new N-acylvinyl derivatives of amino acids |
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| Authors: | Tatyana E Glotova Igor A Ushakov Olga N Kazheva Oleg A Dyachenko Boris A Trofimov |
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| Institution: | a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation
b Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Academician N.N. Semenov Str., Chernogolovka 142432, Russian Federation |
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| Abstract: | The one-pot reaction of natural amino acids (glycine, β-alanine, γ-aminobutyric and ?-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. |
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| Keywords: | Amino acids Acylacetylenes N-Acylvinyl derivatives of amino acids Nucleophilic addition |
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