
%0 Journal Article
%A Allan, RD 
%A Duke, RK 
%A Hambley, TW 
%A Johnston, GAR 
%A Mewett, KN 
%A Quickert, N 
%A Tran, HW 
%T Synthesis of Unsaturated Analogues of Glutamic Acid: Amination of Trianions From Unsaturated Dicarboxylic Acids With Chloramine
%J Australian Journal of Chemistry
%D 1996/07/01
%V 49
%N 7
%P 785-791
%K 
%R https://doi.org/10.1071/CH9960785
%U https://www.publish.csiro.au/paper/CH9960785 
%X Trianions  can be formed from dicarboxylic acids which contain a &#946;,&#947; -double bond, and amination with chloramine yields &#946;,&#947;-unsaturated &#945;-amino acids. This methodology provides a convenient synthesis of amino acids that are inaccessible by other routes. (Z)-3-Phenylthiopent-2-enedioic acid and all four stable unsaturated analogues of the conformationally restricted glutamate analogue 1-aminocyclopentane-1,3-dicarboxylic acid have been synthesized to demonstrate the applicability of the method. The structure of one of the amino acid products, (±)-cis-1-aminocyclopent-4-ene-1,3-dicarboxylic acid (7), has been determined; it crystallizes in the space group P21/c, a 9.245(24), b 8.455(2), c 9.311(3) &#506;, &#946; 95.00(2)&#176;, and the structure was refined to R 0.035 for 980 F. 
