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Stereoselective Synthesis of Monofluoroalkyl α,β-Unsaturated Ketones From Allenyl Carbinol Esters Mediated by Gold and Selectfluor

Zhuang Jin, Rachel S. Hidinger, Bo Xu* and Gerald B. Hammond*

*Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States, Email: Gb.hammondlouisville.edu, bo.xulouisville.edu

Z. Jin, R. S. Hidinger, B. Xu, G. B. Hammond, J. Org. Chem., 2012, 77, 7725-7726.

DOI: 10.1021/jo301239p (free Supporting Information)


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Abstract

Allenyl carbinol esters isomerize to an E,Z mixture of the corresponding dienes in the presence of a gold catalyst. In a subsequent reaction with Selectfluor, this mixture can be converted to monofluoroalkyl α,β-unsaturated ketones with exclusive E selectivity in high yields.

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Key Words

Fluorination, Selectfluor


ID: J42-Y2012-2940