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Base-Catalyzed Stereoselective Isomerization of Electron-Deficient Propargylic Alcohols to E-Enones

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John P. Sonye and Kazunori Koide*

Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260 koide@pitt.edu

J. Org. Chem., 2006, 71 (16), pp 6254–6257

DOI: 10.1021/jo060304p

Publication Date (Web): July 7, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

We have developed highly stereoselective methods to isomerize electron-deficient propargylic alcohols to E-enones under mild conditions (EWG = electron-withdrawing group). Among weak bases we screened, catalytic (10−20 mol %) 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to be effective in most cases. When the substrate is conjugated with an amide, the addition of sodium acetate catalyzed the isomerization.

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