Next Article in Journal
Preparation of Second Generation Ionic Liquids by Efficient Solvent-Free Alkylation of N-Heterocycles with Chloroalkanes
Previous Article in Journal
Antiplatelet Aggregation Coumarins from the Leaves of Murraya omphalocarpa
Molecules 2008, 13(1), 129-148; doi:10.3390/molecules13010129
Article

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

,
,
* ,
 and
Department of Environmental Sciences, University of Milan, Piazza della Scienza, 1, 20126 Milan, Italy
* Author to whom correspondence should be addressed.
Received: 26 November 2007 / Revised: 21 January 2008 / Accepted: 21 January 2008 / Published: 23 January 2008
View Full-Text   |   Download PDF [557 KB, uploaded 18 June 2014]   |  

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.
Keywords: Diastereoselection; enantioselection; lignans; horseradish peroxidase; oxidative Diastereoselection; enantioselection; lignans; horseradish peroxidase; oxidative
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert