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 (free Supporting Information)
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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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