Journal
MOLECULES
Volume 17, Issue 6, Pages 7356-7378Publisher
MDPI
DOI: 10.3390/molecules17067356
Keywords
kinetic resolution; asymmetric esterification; 2-aryl-2-fluoropropanoic acids; fluorinated drugs; 2-fluoroibuprofen; ibuprofen
Funding
- Naito Foundation
- Grants-in-Aid for Scientific Research [22350044, 23655045] Funding Source: KAKEN
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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(2)O) as a coupling agent, bis(alpha-naphthyl) methanol [(alpha-Np)(2)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 alpha-fluorinated drugs containing quaternary carbons at the a-positions in the 2-aryl-2-fluoropropanoic acid structure.
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