Preparation of Substituted Enol Derivatives From Terminal Alkynes and Their Synthetic Utility
John R. DeBergh, Kathleen M. Spivey and Joseph M. Ready*
*Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, Email: joseph.readyutsouthwestern.edu
J. R. DeBergh, K. M. Spivey, J. M. Ready, J. Am. Chem. Soc., 2008, 130, 7828-7829.
DOI: 10.1021/ja803480b (free Supporting Information)
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Stereodefined enol derivatives of aldehydes are prepared from terminal alkynes through Cp2ZrCl2-catalyzed methylalumination and subsequent oxygenation with peroxyzinc species and electrophilic trapping with carboxylic anydrides. The tandem carbometalation/oxygenation tolerates free and protected alcohols, heterocycles, olefins, and nitriles.
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