Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones

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  • Ishizawa Kouhei
    Graduate School of Pharmaceutical Sciences, The University of Tokyo Sohyaku Innovative Research Division, Mitsubishi Tanabe Pharma Corporation
  • Nagai Hideoki
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Shimizu Yohei
    Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Kanai Motomu
    Graduate School of Pharmaceutical Sciences, The University of Tokyo

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Abstract

<p>A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the α-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.</p>

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