Base-Catalyzed Stereoselective Isomerization of Electron-Deficient Propargylic Alcohols to E-Enones
John P. Sonye and Kazunori Koide*
*Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, France, Email: koidepitt.edu
J. P. Sonye, K. Koide, J. Org. Chem., 2006, 71, 6254-6257.
DOI: 10.1021/jo060304p (free Supporting Information)
Catalytic (1,4-diazabicyclo[2.2.2]octane (DABCO) was found to be effective for the isomerization of electron-deficient propargylic alcohols to E-enones under mild conditions. When the substrate is conjugated with an amide, addition of sodium acetate catalyzed the isomerization.
see article for more examples