Breaking Symmetry with Symmetry: Bifacial Selectivity in the Asymmetric Cycloaddition of Anthracene Derivatives

Abstract

Push to activate: A new catalytic strategy for the activation of anthracene derivatives has been developed. From symmetrical starting materials, enantioselective cycloaddition reactions can be achieved by employing a C2-symmetric aminocatalyst. This selectivity is due to the gain or loss of conjugation between the enamine and the anthracene in the two transition-state structures. This methodology is demonstrated in 14 examples with 70–96 % yield and 76–95 % ee. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.