%0 Journal Article
%T Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid
%A Luca Zoia
%A Maurizio Bruschi
%A Marco Orlandi
%A Eeva-Liisa Tolppa
%A Bruno Rindone
%J Molecules
%D 2008
%I MDPI AG
%R 10.3390/molecules13010129
%X Enantiopure chiral amidic derivatives of sinapic acid were oxidised withhydrogen peroxide using horseradish peroxidase (HRP) as the catalyst to give thearyltetraline dilignol thomasidioic acid. Trans-diastereoselectivity and enantioselectivity inthe formation of thomasidioic acid was observed. Computational methods show that theenantioselectivity is controlled by the ¦Â-¦Â oxidative coupling step, while thediastereoselectivity is controlled by the stability of the reactive conformation of theintermediate quinomethide.
%K Diastereoselection
%K enantioselection
%K lignans
%K horseradish peroxidase
%K oxidative
%U http://www.mdpi.com/1420-3049/13/1/129