, Volume 38, Issue 2, pp 129-131
Date: 17 Nov 2012

Zirconocene-promoted synthesis of substituted tetrahydropyrans

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Abstract

Zirconocene reagents derived from zirconocene dichloride and two equivalents of butyllithium react with allylic, homoallylic diene ethers. Hydrolysis of the reaction products yields substituted tetrahydropyrans. The reaction is postulated to occur via cyclization of the diene to form a zirconacyclopentane. This cyclization occurs without allylic rearrangement.