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An improved protocol for the Prins desymmetrization of cyclohexa-1,4-dienes

Butters, Michael, Elliott, Mark Christopher, Hill-Cousins, Joseph Thomas, Paine, James Stephen and Westwood, Alexander William J. 2008. An improved protocol for the Prins desymmetrization of cyclohexa-1,4-dienes. Tetrahedron Letters 49 (28) , pp. 4446-4448. 10.1016/j.tetlet.2008.05.022

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Improved conditions are reported for the Prins-pinacol rearrangement of cyclohexa-1,4-diene-derived acetals. The use of triflic acid gives particularly clean reaction, resulting in a mixture of regioisomers in an approximately 10:1 ratio. A tethered version of this reaction is also reported, giving a tricyclic compound with the same stereochemistry as the core of the cladiellin diterpenes.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4039
Last Modified: 02 Jan 2018 21:20

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