Reactive diene for synthesis of substituted catechols

A new 5,6-dimethylene-1,4-dioxane has proven to be a very reactive diene in Diels–Alder reactions. Reaction with acetylenic dienophiles provides a route to substituted catechols. (2 R,3 R)-2,3-Dimethoxy-2,3-dimethyl-5,6-dimethylene-1,4-dioxane has been synthesized and is a highly efficient diene in...

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Bibliographic Details
Published in:Tetrahedron letters 2008-01, Vol.49 (2), p.219-221
Main Authors: Compton, Benjamin J., Larsen, David S., Larsen, Lesley, Weavers, Rex T.
Format: Article
Language:English
Subjects:
Cisoid diene
Diels–Alder
Protected catechol
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Summary:A new 5,6-dimethylene-1,4-dioxane has proven to be a very reactive diene in Diels–Alder reactions. Reaction with acetylenic dienophiles provides a route to substituted catechols. (2 R,3 R)-2,3-Dimethoxy-2,3-dimethyl-5,6-dimethylene-1,4-dioxane has been synthesized and is a highly efficient diene in Diels–Alder reactions. Reaction with acetylenic dienophiles provides a simple route to substituted catechols. Reactions with some ethylenic dienophiles are also reported.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.11.085