Enantiopure chiral amidic derivatives of sinapic acid were oxidised with hydrogen peroxide using horseradish peroxidase (HRP) as the catalyst to give the aryltetraline dilignol thomasidioic acid. Trans-diastereoselectivity and enantioselectivity in the formation of thomasidioic acid was observed. Computational methods show that the enantioselectivity is controlled by the beta-beta oxidative coupling step, while the diastereoselectivity is controlled by the stability of the reactive conformation of the intermediate quinomethide.
Zoia, L., Bruschi, M., Orlandi, M., Tolppa E-L, & Rindone, B. (2008). Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid. MOLECULES, 13(1), 129-148 [10.3390/molecules13010129].
Citazione: | Zoia, L., Bruschi, M., Orlandi, M., Tolppa E-L, & Rindone, B. (2008). Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid. MOLECULES, 13(1), 129-148 [10.3390/molecules13010129]. | |
Tipo: | Articolo in rivista - Articolo scientifico | |
Carattere della pubblicazione: | Scientifica | |
Titolo: | Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid | |
Autori: | Zoia, L; Bruschi, M; Orlandi, M; Tolppa E-L; Rindone, B | |
Autori: | ||
Data di pubblicazione: | gen-2008 | |
Lingua: | English | |
Rivista: | MOLECULES | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.3390/molecules13010129 | |
Appare nelle tipologie: | 01 - Articolo su rivista |