Reversal of the regioselectivity in a cycloaddition of o-quinones by varying the position of alkoxy substituents

The cycloaddition of o-quinones with the protected sinapyl alcohol proceeded regioselectively to afford the 1,4-benzodioxanes. We have investigated the regioselective cycloaddition of o-quinones 1b– e with the protected sinapyl alcohol 2. It was found that the position of the alkoxy substituent on t...

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Bibliographic Details
Published in:Tetrahedron letters 2008-04, Vol.49 (16), p.2558-2561
Main Authors: Kuboki, Atsuhito, Yamamoto, Toru, Taira, Mamie, Arishige, Tetsuya, Konishi, Rina, Hamabata, Mami, Shirahama, Mutsumi, Hiramatsu, Takeya, Kuyama, Kohei, Ohira, Susumu
Format: Article
Language:English
Subjects:
1,4-Benzodioxane
Cycloaddition
o-Quinone
Regioselectivity
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Summary:The cycloaddition of o-quinones with the protected sinapyl alcohol proceeded regioselectively to afford the 1,4-benzodioxanes. We have investigated the regioselective cycloaddition of o-quinones 1b– e with the protected sinapyl alcohol 2. It was found that the position of the alkoxy substituent on the o-quinone ring controlled the regioselectivity of the cycloaddition. In addition, our reported procedure for determining the location of the side chains on 1,4-benzodioxanes has been improved.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.02.109