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We report a new method for the preparation of chiral 2-aryl-2-fluoropropanoic acids, including 2-fluoroibuprofen, a fluorinated analogue of non-steroidal anti-inflammatory drugs (NSAIDs), by the kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids using enantioselective esterification. By applying pivalic anhydride (Piv<sub>2</sub>O) as a coupling agent, bis(<em>α</em>-naphthyl)methanol [(<em>α</em>-Np)<sub>2</sub>CHOH] as an achiral alcohol, and (+)-benzotetramisole (BTM) as a chiral acyl-transfer catalyst, a series of racemic 2-aryl-2-fluoropropanoic acids were kinetically separated to afford the optically active carboxylic acids and the corresponding esters with good to high enantiomeric excesses. This technology can provide a convenient approach to furnish the chiral <em>α</em>-fluorinated drugs containing quaternary carbons at the <em>α</em>-positions in the 2-aryl-2-fluoropropanoic acid structure.