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Issue 29, 2012
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Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction

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Abstract

The first enantioselective Reformatsky-type reaction of ethyl iodofluoroacetate has been accomplished with alkyl aryl ketones. High diastereoselectivities and excellent enantioselectivities for the major diastereomer (93–95% ee) were achieved with large alkyl groups. For smaller alkyl groups the diastereoselectivities were moderate, but excellent enantioselectivities were obtained for both diastereomers (79–94% ee).

Graphical abstract: Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction

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Publication details

The article was received on 21 Dec 2011, accepted on 02 Feb 2012 and first published on 02 Feb 2012


Article type: Communication
DOI: 10.1039/C2CC17985G
Citation: Chem. Commun., 2012,48, 3500-3502
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    Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction

    M. Fornalczyk, K. Singh and A. M. Stuart, Chem. Commun., 2012, 48, 3500
    DOI: 10.1039/C2CC17985G

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