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

Longwu Ye, Weimin He and Liming Zhang*

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

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

DOI: 10.1021/ja1033952 (free Supporting Information)


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Abstract

A general synthesis of various oxetan-3-ones uses readily available propargylic alcohols as substrates and proceeds without the exclusion of moisture or air. The facile formation of the strained oxetane ring provides strong support for the intermediacy of α-oxo gold carbenes. This safe and efficient generation of gold carbenes offers an entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.

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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

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


Key Words

O-Heterocycles, Pyridine N-Oxides


ID: J48-Y2010-1780