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Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Brønsted Acid Catalyst
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    Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Brønsted Acid Catalyst
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    Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2017, 139, 25, 8424–8427
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    https://doi.org/10.1021/jacs.7b04795
    Published May 30, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    A chiral magnesium potassium binaphthyldisulfonate cluster, as a chiral Brønsted acid catalyst, was shown to catalyze an enantioselective cycloaddition of styrenes with aldimines for the first time. The strong Brønsted acidity of the catalyst precursors, which might dissolve drying agents and take up the leached Mg2+ and K+, serendipitously led to good enantioselectivity. Mechanistic aspects were supported by X-ray and ESI-MS analysis of the catalyst and a kinetics study of the reaction. Useful transformations to optically active 1,3-amino alcohols on a gram scale were also demonstrated.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.7b04795.

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    • X-ray crystallographic data for 4j (CIF)

    • X-ray crystallographic data for 1,3-syn-2,3-anti-12 (CIF)

    • X-ray crystallographic data for 22 (CIF)

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    Cited By

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2017, 139, 25, 8424–8427
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.7b04795
    Published May 30, 2017
    Copyright © 2017 American Chemical Society

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