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Molecules 2008, 13(1), 129-148; https://doi.org/10.3390/molecules13010129

Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid

Department of Environmental Sciences, University of Milan, Piazza della Scienza, 1, 20126 Milan, Italy
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Received: 26 November 2007 / Revised: 21 January 2008 / Accepted: 21 January 2008 / Published: 23 January 2008
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Abstract

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 β-β oxidative coupling step, while thediastereoselectivity is controlled by the stability of the reactive conformation of theintermediate quinomethide. View Full-Text
Keywords: Diastereoselection; enantioselection; lignans; horseradish peroxidase; oxidative Diastereoselection; enantioselection; lignans; horseradish peroxidase; oxidative
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Zoia, L.; Bruschi, M.; Orlandi, M.; Tolppa, E.-L.; Rindone, B. Asymmetric Biomimetic Oxidations of Phenols: The Mechanism of the Diastereo- and Enantioselective Synthesis of Thomasidioic Acid. Molecules 2008, 13, 129-148.

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