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Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyaura Cross-Coupling Reactions

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    Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyaura Cross-Coupling Reactions
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    § Department of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario K7L 3N6, Canada
    Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
    [email protected]
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    Cite this: J. Am. Chem. Soc. 2014, 136, 16, 5828–5831
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    https://doi.org/10.1021/ja412159g
    Published March 31, 2014
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    Abstract

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    The Suzuki–Miyaura cross-coupling of chiral, enantiomerically enriched dibenzylic boronic esters is described. The reaction proceeds with almost complete retention of stereochemistry, providing access to triarylmethanes, compounds that have high biological activity and are difficult to prepare in enantiomerically pure form using other methods.

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    Spectral data, experimental procedures, X-ray crystallographic data, and detailed information on the assignment of stereochemistry. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2014, 136, 16, 5828–5831
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