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Issue 11, 2006
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Highly diastereoselective Diels–Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone

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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


Submitted
14 Mar 2006
Accepted
13 Apr 2006
First published
08 May 2006

Org. Biomol. Chem., 2006,4, 2296-2303
Article type
Paper

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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