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

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
* Author to whom correspondence should be addressed.
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)
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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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