Reagent-induced asymmetric induction in addition reaction of reduced glutathione onto bis-Mannich chalcones
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2018
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The stereochemistry of non-enzyme catalyzed nucleophilic addition of GSH to 4′-hydroxychalcone 1 and its bis-Mannich derivative 2 was investigated at different pH values (pH 3.2, 6.1, 7.4, and 8.0). The stereochemical outcome of the reactions was evaluated by HPLC-UV-Vis method. Under strongly acidic conditions (pH 3.2), an unexpected diastereoselective addition of GSH onto the bis-Mannich derivative 2 was observed. Such a selectivity could not be observed in the similar reaction of 2 with N-acetylcysteine. The observed stereoselectivity can be rationalized by ion-pair formation between the protonated Mannich nitrogens and the deprotonated GSH(glutamate)-carboxylate. To the best of our knowledge, this is the first example of reagent-induced asymmetric induction in Michael-type additions of thiols.
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Chalcones, Glutathione, Michael reaction, Reagent-controlled asymmetric addition
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BERNARDES, Aline et al. Reagent-induced asymmetric induction in addition reaction of reduced glutathione onto bis-Mannich chalcones. Archiv der Pharmazie: Chemistry in Life Sciences, Weinheim, v. 351, n. 7, e1700386, 2018. DOI: 10.1002/ardp.201700386. Disponível em: https://onlinelibrary.wiley.com/doi/10.1002/ardp.201700386. Acesso em: 17 ago. 2023.