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Resolution of Carboxylic Acids Using Copper(I)-Promoted Removal of Propargylic Esters under Neutral Conditions
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    Resolution of Carboxylic Acids Using Copper(I)-Promoted Removal of Propargylic Esters under Neutral Conditions
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    Chemical Methodologies and Library Development Center, Delbert M. Shankel Structural Biology Center, 2034 Becker Drive, University of Kansas, Lawrence, Kansas 66047-3761, United States
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 10, 4168–4172
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    https://doi.org/10.1021/jo200433w
    Published April 14, 2011
    Copyright © 2011 American Chemical Society

    Abstract

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    A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ≥94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conventional ester hydrolysis.

    Copyright © 2011 American Chemical Society

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    Supporting Information

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    Copies of 1H and 13C NMR spectra for new compounds and chiral HPLC data and X-ray data for the derivative of compound 9. This material is available free of charge via the Internet at http://pubs.acs.org.

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    6. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. Copper( I ) Chloride. 2017https://doi.org/10.1002/9780471264194.fos02876.pub6
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    12. Partha Ghosh, Jeffrey Aube. ChemInform Abstract: Resolution of Carboxylic Acids Using Copper(I)‐Promoted Removal of Propargylic Esters under Neutral Conditions.. ChemInform 2011, 42 (33) https://doi.org/10.1002/chin.201133021

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 10, 4168–4172
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo200433w
    Published April 14, 2011
    Copyright © 2011 American Chemical Society

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