
TY  - JOUR
A1  - Allan, RD 
A1  - Duke, RK 
A1  - Hambley, TW 
A1  - Johnston, GAR 
A1  - Mewett, KN 
A1  - Quickert, N 
A1  - Tran, HW 
T1  - Synthesis of Unsaturated Analogues of Glutamic Acid: Amination of Trianions From Unsaturated Dicarboxylic Acids With Chloramine
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 7
SP  - 785
EP  - 791
KW  - 
UR  - https://doi.org/10.1071/CH9960785 
N2  - 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. 
ER  -

