@misc{folikumah_thiol_michaeltype_2019, author={Folikumah, M., Neffe, A., Behl, M., Lendlein, A.}, title={Thiol Michael-Type Reactions of Optically Active Mercapto-Acids in Aqueous Medium}, year={2019}, howpublished = {journal article}, doi = {https://doi.org/10.1557/adv.2019.308}, abstract = {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.}, note = {Online available at: \url{https://doi.org/10.1557/adv.2019.308} (DOI). Folikumah, M.; Neffe, A.; Behl, M.; Lendlein, A.: Thiol Michael-Type Reactions of Optically Active Mercapto-Acids in Aqueous Medium. MRS Advances. 2019. vol. 4, no. 46 - 47, 2515-2525. DOI: 10.1557/adv.2019.308}}