Synthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross-Coupling

Authors

  • Jeffrey L. Gustafson,

    1. Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107 (USA), Fax: (+1) 203-496-4900
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  • Dr. Daniel Lim,

    1. Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107 (USA), Fax: (+1) 203-496-4900
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  • Kimberly T. Barrett,

    1. Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107 (USA), Fax: (+1) 203-496-4900
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  • Prof. Dr. Scott J. Miller

    Corresponding author
    1. Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107 (USA), Fax: (+1) 203-496-4900
    • Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107 (USA), Fax: (+1) 203-496-4900
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  • We are grateful to the National Institute of General Medical Sciences of the National Institutes of Health (GM-068649) for support.

Abstract

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A selective sequence: An enantioselective synthesis (see scheme) of atropisomerically defined p-terphenyls, as well as tetra- and pentaaryl compounds is reported. The synthesis proceeds through sequential atropisomer-selective electrophilic aromatic substitution and regioselective palladium-catalyzed cross-coupling reactions.

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