Issue 11, 2006
From the journal:

Organic & Biomolecular Chemistry

Highly diastereoselective Diels–Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone

Harry Adams,a   Simon Jones*a  and  Isaac Ojea-Jimeneza  

* Corresponding authors

a Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, UK
E-mail: simon.jones@sheffield.ac.uk
Fax: +44 (0)114 222 9346
Tel: +44 (0)114 222 9483

Abstract

Diels–Alder cycloadditions of p-benzoquinone with 9R-(1-methoxyethyl)anthracene provides a 60 : 40 ratio of cycloadducts when heated at reflux in xylene. Mechanistic studies to explore the origins of this selectivity have shown that at lower temperatures the kinetic product predominates, giving a 96 : 4 ratio of cycloadducts.

Graphical abstract: Highly diastereoselective Diels–Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone

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Article information

DOI
https://doi.org/10.1039/B603819K
Article type
Paper
Submitted
14 Mar 2006
Accepted
13 Apr 2006
First published
08 May 2006

Org. Biomol. Chem., 2006,4, 2296-2303

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Highly diastereoselective Diels–Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone

H. Adams, S. Jones and I. Ojea-Jimenez, Org. Biomol. Chem., 2006, 4, 2296 DOI: 10.1039/B603819K

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