Chemoselective Synthesis of β-Ketophosphonates Using Lithiated α-(Trimethylsilyl)methylphosphonate

Simon Specklin* and Janine Cossy*

*Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231-ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France, Email: simon.specklinespci.fr, janine.cossyespci.fr

S. Specklin, J. Cossy, J. Org. Chem., 2015, 80, 3302-3308.

DOI: 10.1021/acs.joc.5b00039

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Abstract

The use of lithiated methyl α-(trimethylsilyl)methylphosphonate as mild lithiated phosphonate reagent enables a highly chemoselective synthesis of β-ketophosphonates from pentafluorophenyl esters in high yield. The reaction tolerates for example the presence of unactivated esters.

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Key Words

phosphonates

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ID: J42-Y2015