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Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones

Longwu Ye, Li Cui, Guozhu Zhang and Liming Zhang*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, Email: zhangchem.ucsb.edu

L. Ye, L. Cui, G. Zhang, L. Zhang, J. Am. Chem. Soc., 2010, 132, 3258-3259.

DOI: 10.1021/ja100041e (free Supporting Information)


Abstract

An expedient and reliable method for accessing reactive α-oxo gold carbenes via gold-catalyzed intermolecular oxidation of terminal alkynes offers a safe and economical alternative to strategies based on diazo substrates. Its synthetic potential is demonstrated by expedient preparation of dihydrofuran-3-ones containing a broad range of functional groups.


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Gold-Catalyzed One-Step Practical Synthesis of Oxetan-3-ones from Readily Available Propargylic Alcohols

L. Ye, W. He, L. Zhang, J. Am. Chem. Soc., 2010, 132, 8550-8551.


Key Words

O-Heterocycles, Ketones, Pyridine N-Oxide


ID: J48-Y2010-0550