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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 4
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Original Articles

Alkenyl-Substituted Ketals as Efficient Precursors to Claisen Rearrangement Substrates

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Pages 663-672 | Received 16 Sep 1996, Published online: 20 Aug 2006
 

Abstract

Alkenyl-substituted ketals 6 readily afford Claisen rearrangement substrates 7 upon treatment with TESOTf/DIPEA. Thermal rearrangement completes this efficient and general process for generation of functionally rich ϵ-oxy-γ,δ-enones 8.

Notes

Daub and coworkers have investigated the regio- and stereoselectivity of

ketal-Claisen rearrangements of unsymmetrical enol ethers i and ii.

Additional information

Notes on contributors

Hemaka A. Rajapakse

Dedicated to Professor Frederick B. Stocker on the occasion of his retirement.

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