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Isothiourea-Catalyzed Asymmetric Synthesis of β-Lactams and β-Amino Esters from Arylacetic Acid Derivatives and N-Sulfonylaldimines
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    Isothiourea-Catalyzed Asymmetric Synthesis of β-Lactams and β-Amino Esters from Arylacetic Acid Derivatives and N-Sulfonylaldimines
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    EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, U.K.
    GSK, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, U.K.
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2014, 79, 4, 1626–1639
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    https://doi.org/10.1021/jo402590m
    Published January 16, 2014
    Copyright © 2014 American Chemical Society

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    The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereodefined 2,3-diaryl-β-amino esters (after ring-opening) and 3,4-diaryl-anti-β-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the β-lactam framework was possible without racemization by treatment with SmI2.

    Copyright © 2014 American Chemical Society

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    1H and 13C{1H} NMR spectra and HPLC traces of all products. X-ray crystallographic data for anti-17 (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2014, 79, 4, 1626–1639
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo402590m
    Published January 16, 2014
    Copyright © 2014 American Chemical Society

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