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., & 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].
Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid
ZOIA, LUCA;BRUSCHI, MAURIZIO;ORLANDI, MARCO EMILIO;TOLPPA, EEVA-LIISA;RINDONE, BRUNO
2008-01
Abstract
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.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
