Next Article in Journal
Substituted Benzamides Containing Azaspiro Rings as Upregulators of Apolipoprotein A-I Transcription
Next Article in Special Issue
Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst
Previous Article in Journal
Ring-Expansion Reaction of Oximes with Aluminum Reductants
Previous Article in Special Issue
Cooperative Al(Salen)-Pyridinium Catalysts for the Asymmetric Synthesis of trans-Configured β-Lactones by [2+2]-Cyclocondensation of Acylbromides and Aldehydes: Investigation of Pyridinium Substituent Effects
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

 and *
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 / Revised: 4 June 2012 / Accepted: 8 June 2012 / Published: 14 June 2012
(This article belongs to the Special Issue Asymmetric Catalysis)
Download PDF [606 KB, uploaded 18 June 2014]
SciFeed

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 kinetic resolution; asymmetric esterification; 2-aryl-2-fluoropropanoic acids; fluorinated drugs; 2-fluoroibuprofen; ibuprofen
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert