Asymmetric Synthesis of 2-Aryl-5-oxotetrahydrofuran-2-carboxylic Acids

Artur Jõgi; Anne Paju; Tõnis Pehk; Tiiu Kailas; Aleksander-Mati Müürisepp; Tõnis Kanger; Margus Lopp

doi:10.1055/s-2006-950193

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Synthesis 2006(18): 3031-3036
DOI: 10.1055/s-2006-950193

PAPER

Asymmetric Synthesis of 2-Aryl-5-oxotetrahydrofuran-2-carboxylic Acids

Artur Jõgi^a, Anne Paju^a, Tõnis Pehk^b, Tiiu Kailas^a, Aleksander-Mati Müürisepp^a, Tõnis Kanger^a, Margus Lopp*^a
^a Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia
Fax: +372(6)202828; e-Mail: lopp@chemnet.ee;
^b National Institute of Chemical Physics and Biophysics, Akadeemia tee 23, Tallinn 12618, Estonia

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Publication History

Received 7 April 2006
Publication Date:
15 August 2006 (online)

Abstract
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Abstract

3-Aryl-2-hydroxycyclopent-2-en-1-ones, when subjected to asymmetric oxidation, result in enantiomerically enriched 2-aryl-5-oxotetrahydrofuran-2-carboxylic acids. Electron-donating substituents in the para position of the phenyl ring increase the yield and decrease the enantioselectivity of the process.

Key words

tertiary γ-lactones - oxotetrahydrofuran-2-carboxylic acids - asymmetric oxidations - stereoselectivity

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