%0 journal article
%@ 2059-8521
%A Folikumah, M., Neffe, A., Behl, M., Lendlein, A.

%D 2019
%J MRS Advances
%N 46 - 47
%P 2515-2525 
%R doi:10.1557/adv.2019.308
%T Thiol Michael-Type Reactions of Optically Active Mercapto-Acids in Aqueous Medium
%U https://doi.org/10.1557/adv.2019.308
46 - 47 
%X In model reactions were investigated the kinetics, the specificity and influence of stereochemistry of this reaction. We could show that only reactions involving SH-Leu yielded the expected thiol-Michael product. The inability of SH-Phe to react was attributed to the steric hindrance of the bulky phenyl group. In aqueous media, successful reaction using SH-Leu is thought to proceed via the sodium salt formed in-situ by the addition of NaOH solution, which was intented to aid the solubility of the mercapto-acid in water. Fast reaction rates and complete acrylate/maleimide conversion were only realized at pH 7.2 or higher suggesting the possible use of SH-Leu under physiological conditions for thiol Michael-type reactions. This method of in-situ formed alkali salts could be used as a fast approach to screen mercapto-acids for thio Michael-type reactions without the synthesis of their corresponding esters.