%0 Journal Article
%T Application of Glaser¨CHay Diyne Coupling To Constrain N¦Á-Amino Acid Amides via a N¨CN Bridge
%J -
%D 2019
%R https://doi.org/10.1021/acscombsci.8b00179
%X We present the application of a Glaser¨CHay diyne coupling for the synthesis of conformationally constrained N¦Á-amino acid amides with different diyne ring sizes. Twelve-membered rings were the smallest rings that could be prepared by this approach. We observed the formation of triethylammonium adducts in the cases of smaller (10- and 11-membered) rings. Calculation of the conformational barriers for the cyclization reactions of various ring sizes demonstrated that the formation of amino acid-derived smaller rings by this reaction is thermodynamically unfavorable
%U https://pubs.acs.org/doi/10.1021/acscombsci.8b00179