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

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Abstract

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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Key Words

acylation, carbonyl compounds (alkylation, oxidation), tert-butyl hydroperoxide

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ID: J48-Y2008-1670