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.
Articolo in rivista - Articolo scientifico
Scientifica
enantioselection; lignans; horseradish peroxidase; oxidative phenol coupling; conformational analysis; semiempiric calculations
English
129
148
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].
Zoia, L; Bruschi, M; Orlandi, M; Tolppa, E; Rindone, B
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/3868
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