Molecules 2012, 17(6), 7356-7378; doi:10.3390/molecules17067356
Article

A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids

Received: 2 May 2012; in revised form: 4 June 2012 / Accepted: 8 June 2012 / Published: 14 June 2012
(This article belongs to the Special Issue Asymmetric Catalysis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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 (Piv2O) as a coupling agent, bis(α-naphthyl)methanol [(α-Np)2CHOH] 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 α-fluorinated drugs containing quaternary carbons at the α-positions in the 2-aryl-2-fluoropropanoic acid structure.
Keywords: kinetic resolution; asymmetric esterification; 2-aryl-2-fluoropropanoic acids; fluorinated drugs; 2-fluoroibuprofen; ibuprofen
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MDPI and ACS Style

Tengeiji, A.; Shiina, I. A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids. Molecules 2012, 17, 7356-7378.

AMA Style

Tengeiji A, Shiina I. A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids. Molecules. 2012; 17(6):7356-7378.

Chicago/Turabian Style

Tengeiji, Atsushi; Shiina, Isamu. 2012. "A New Method for Production of Chiral 2-Aryl-2-fluoropropanoic Acids Using an Effective Kinetic Resolution of Racemic 2-Aryl-2-fluoropropanoic Acids." Molecules 17, no. 6: 7356-7378.

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