1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses

Date

2005

Authors

Avery, T.
Caiazza, D.
Culbert, J.
Taylor, D.
Tiekink, E.

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Journal of Organic Chemistry, 2005; 70(21):8344-8351

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Thomas D. Avery, Daniela Caiazza, Julie A. Culbert, Dennis K. Taylor, and Edward R. T. Tiekink

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Abstract

A new method for the construction of tetrahydropyrans derived from readily available 1,2-dioxines containing a tethered hydroxyl moiety is described. The reaction proceeds via a base-catalyzed rearrangement of the 1,2-dioxines to either the isomeric cis or trans -hydroxy enones followed by intramolecular oxa-Michael addition of the tethered hydroxyl group.

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Copyright © 2005 American Chemical Society

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